


30 Days of Destiel

by Krislmart



Category: Supernatural
Genre: 1950s Slang, Alternate Universe - 1950s, Alternate Universe - College/University, Alternate Universe - Pirate, Angst, Awkwardness, Baking, Ballroom Dancing, Bars and Pubs, Canon Temporary Character Death, Castiel (Supernatural) Loves Coffee, Coffee, Costume Parties & Masquerades, Dean Winchester Does Karaoke, Dean Winchester Loves Pie, Dean Winchester Loves The Impala, Death, Fights, First Kiss, Fluff, Forgetting, Fourth of July, Gaming, Human Castiel (Supernatural), Hurt/Comfort, Ice Skating, Indiana Jones References, Just a touch of smut, Karaoke, Knight Castiel (Supernatural), LARPer Dean Winchester, LARPing, Light Angst, M/M, Mario Kart, Milkshakes, NSFW, Picnics, Pie, Princess - Freeform, Princess Dean Winchester, Purgatory, Raiders of the Lost Ark - Freeform, Romance, Romantic Comedy, Sharing Clothes, Shipper Sam Winchester, Smut, Snapchat, Stargazing, Temporary Character Death, The Impala (Supernatural), Twister - Freeform, Ugly Holiday Sweaters, Ugly Sweaters, Umbrellas, Waltzing, Water Fight, Wedding Fluff, Weddings, damnatio memoriae, movies - Freeform, selfie - Freeform, sword fight
Language: English
Status: Completed
Published: 2019-04-06
Updated: 2019-05-14
Packaged: 2020-01-05 12:13:49
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 30
Words: 25,405
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/18365795
Author URL: https://archiveofourown.org/users/Krislmart/pseuds/Krislmart
Summary: April 1 - A selfie together





	1. Day 1 - Snapchat selfies

**Author's Note:**

> This is my first attempt at a fic challenge and my first ever posted fanfic :D

“What the hell are you doing?” Dean stared at Castiel, who was squinting at his phone, tilting his head from side to side.

“I’m trying to figure out how to get dog ears,” Castiel matter-of-factly responded, not even bothering to look up at Dean.

Dean dragged a chair out from the library table, beer bottle thunking down on the surface. “Run that by me again? Why do you need dog ears?”

“Not in real life, Dean.” Cas looked up at him with a resigned look on his face. “Claire said that everyone uses this Snapchat app to communicate now and she downloaded it on my phone. Unfortunately, she didn’t have time to explain it. We’ve been exchanging these photos and her last one had dog ears.  She claims it’s a ‘filter’ but I don’t understand how she did it.”

Dean shook his head at Cas’ air quotes and popped the cap off his beer bottle. “‘Fraid I won’t be much help for you Cas. Sammy might can help you but all this social media crap,” he gestured towards Cas’ phone with his bottle, “is beyond me.”

“Sam told me that he may technically be a millennial but he wasn’t Google.” Cas frowned to himself. “He seemed a little irritable and I didn’t want to press the issue.”

Dean kicked his heels out under the table and leaned back. “Who knows with Sam? But have you tried Googling it?”

“Well,” Cas hesitated. “I have. But it’s hard to read the article and also look at the app at the same time when they’re both on the same phone.”

A smile tugged at Dean’s lips. Scooting his chair closer to Cas, he pulled his own phone out. “Alright, buddy, we can figure this out.”

A ding came from Cas’ phone. He unlocked the phone and opened Snapchat. “This square is purple instead of red,” he mused aloud as he clicked on it. Claire’s face popped up with giant bunny ears coming out of her head. “Hi Castiel,” she laughed in a high-pitched voice. “Are you having trouble figuring out Snapchat?”

“You can send videos, too?” Cas’ eyebrows scrunched together.

Dean quickly typed “how to use snapchat” into Google. He clicked on the first article but shook his head at the lengthy introductions. “I just want a damn tutorial.”

Finally, he found a site that broke everything down in simple steps. He turned Cas’ phone toward him and clicked the the smiley face beside the shutter button. “Turn the front-facing camera on, Cas.”

As soon as the camera flipped, Dean started sliding through the array of filters at the bottom of the screen. He stifled a laugh as large dog ears appeared on Cas’ head. “Go ahead and pick one, Cas. If you want to send a video, you have to press and hold the button.” Dean turned his attention back to his phone. 

“Hello Claire,”Cas started. “I am not having trouble with Snapchat. Dean helped me. Isn’t that right Dean?”

Dean looked up, only to see the dog ears on his face. “Ah come on man. I look ridiculous.”

“I can delete it,” Cas said softly. His finger moved to the top left of the screen.

“Wait,” Dean blurted out. “You can send it, that’s fine. But, maybe…” he trailed off.

“Would you also like to take a flattering video?” Cas asked.

“Or maybe we can just take a picture together? That would work too.” Dean avoided Cas’ eyes.

“I would like that,” Cas smiled.

Dean scooted his chair back close to Cas. He leaned over his shoulder as Cas flipped through the filters again. “What about this one?” 

Dean leaned closer and smirked. The two of them had flower crowns on. “Sure, why not Cas?” He gave the camera his best blue steel but, before Cas snapped the picture, he saw Cas’ stoic expression. Gently, he elbowed Cas in the ribs. “Taking a picture that painful, Cas?”

Cas glanced at him and then back at the camera. Slowly, a warm smile crept across his features. Dean felt himself start to grin as he looked back at the camera.  _ Click _ .

Dean kept smiling as he studied the photo. “Can you save that, Cas?”

Cas bit his lip. “I’m not sure how, Dean.”

“Well go ahead and send that to Claire, but,” he reached for his own phone. “How about we take a regular photo on my phone?”

“I believe it’s called a selfie.” Cas gave Dean a gummy smile.

“Alright, alright, get over here.” Dean hooked his chin over Cas’ shoulder and grinned at the camera before clicking the shutter.  _ It might be time to change my wallpaper _ , he thought to himself, grin stretching even wider. 


	2. Day 2 - The milkshake holds the answers

**Summary for the Chapter:**

> April 2 - Sharing a milkshake

Sam had noticed something  _ off  _ about his brother the last few weeks. It wasn’t anything bad really, just off. 

About two weeks ago, Sam first noticed the whistling. Now, Dean had always had a penchant for whistling, especially when he was working on something or trying to distract himself. But this whistling was different. Sam could have sworn that his brother only knew rock songs that were older than Sam. Sam had heard them played, over and over again, throughout the years in the Impala. These songs were different, though. 

When Dean wasn’t looking, Sam held his phone under the table, recording the whistling. 

The next day, when Dean was out on a beer run and Cas was nowhere to be seen, Sam played the recording, trying to figure out the song but it wasn’t ringing a bell. On a whim, he texted Charlie.

Sam: Hey, do you think you can figure out the name of a song from someone whistling it?

Charlie: I can try. Send me the file and I’ll see what I can do. Is this for a case?

Sam: Kind of? It’s hard to explain.

In less than ten minutes, his ringtone broke the bunker’s silence.

“Dude, what kind of monster hums ‘Love Me Like You Do?’” Charlie burst out.

“That’s the name of the song? Never heard it before,” Sam mused.

“Of course not. It’s a love song from the 50 Shades movie. Definitely out of your wheelhouse. Laters bitches!” 

_ A love song? Weird _ . Sam shrugged and turned back to the case research.

The next weird thing wouldn’t normally be weird but, looking back, it strengthened Sam’s case.

Dean was being weird about his phone. He had never really cared about leaving it in the car or on the bedside table in the motel. Now, however, the phone was glued to Dean’s hand. Not only was he always near it, but he would continuously smile at the phone.

Right now was a perfect example. The two of them were in a diner, killing time until they could visit the morgue. Dean’s phone kept buzzing beside his plate. Instead of letting it wait until he inhaled his burger, Dean would answer every single buzz. A dopey grin kept crossing his face and once, a faint blush covered the tops of his ears.

Sam thought about calling his brother out but, like a snake in the grass, decided to bide his time and get more evidence.

The most crucial piece of evidence had just clicked into place today. The two of them had tackled a case out in Costa Mesa, California. All Sam really wanted to do was head for home, or at least off the West Coast. It had been years but sometimes just being in California, especially on warm, beautiful days, was enough to bring memories of Jess back. Dean, however, kept talking about some amazing milkshakes that they just had to try.

“Come on Sammy, they were ranked number one online. You can eat a bunch of kelp and run day and night to make up for it. Please?” Dean widened his eyes, trying his best approximation of Sam’s puppy dog eyes.

“Fine,” Sam grumbled.

“I’m gonna call Cas. The dude should experience an epic milkshake, too, ya know?” Dean flipped his phone open and pressed one button.

“Hey Cas, you should meet us at The Straw in Costa Mesa. … No there isn’t a demon there. … There’s nothing bad. ...They have amazing milkshakes, Cas. … One milkshake won’t do that. … Cas, it’s a song, not fact. Just meet us there, okay?”

Sam felt a grin tugging at his lips. He could only imagine what the other half of that conversation had been. 

When they pulled into the parking lot, they saw Cas standing outside. The three of them filed in and stared in awe at the variety of milkshake options. Sam ended up choosing The Campfire and, after going back and forth several times, Dean chose La Bella Donna.

Sam raised his eyebrow at the more plain choice but shrugged. Cas had already snagged a table.

“Where’s your milkshake, Cas?” Sam asked.

“I don’t really need a milkshake, Sam. I’m not going to enjoy it in the same way.” Cas fiddled with the edge of a napkin.

Dean slid into the seat beside Cas. “Here ya go, Cas,” he smiled. “I know all you taste is molecules but I figured you could have a few sips of mine. Milkshake this good you can’t pass it up. Plus, it’s got coffee in it. That’s your favorite, ya know.” Sam’s eyebrows rose higher at Dean’s rambling.

“You want to share your milkshake with me?” Cas softly asked.

“Well, yeah. Unless you don’t..” Dean mumbled.

A gummy smile split Cas’ face. “I would love to share a milkshake with you, Dean.”

Sam noticed the tops of Dean’s ears were flushed red and he smiled to himself. He couldn’t help but tease his older brother a little. “Dean, aren’t you worried about all the boys?”

“See!” Cas blurted out. “Even Sam knows about milkshakes bringing the boys to the yard. Is this going to be a problem, Dean? We should prepare.”

“If you need a milkshake to get a guy, then clearly you’re doing it wrong,” Dean laughed.

“Well, you brought me here for a milkshake,” Cas countered.

“I -- well, I ---,” Dean spluttered.

Cas grinned as he took a sip of the milkshake. “These molecules are actually pleasant together.”

**Notes for the Chapter:**

> So the milkshake place I mentioned here is an actual restaurant in California and the photos and descriptions of their milkshakes looked heavenly!


	3. Day 3 - Never forget the coffee

**Summary for the Chapter:**

> April 3 - Grumpy morning heads

Ever since Castiel fell, mornings were Dean’s favorite time of the day. It was odd, at first, seeing Castiel wander the bunker at all hours of the night to not seeing him until at least ten in the morning. 

Dean always got a small chuckle out of watching Cas slump into the kitchen, focus solely on the coffee machine sitting in the corner. Getting in between Cas and coffee these mornings would earn you a smite-worthy glare. 

Carefully filling the pot up, Dean thought back to last week when they didn’t make their usual grocery run in time.

Dean had decided to stay in bed for a little longer that morning. He and Sam had just gotten back from a rough hunt the previous morning and had spent a good chunk of the day refilling ammo boxes and cleaning their gear. It had been a particularly messy nest of vamps and they had to take out a shapeshifter on the way back home. Because of that, neither of them went back out to Smith’s Center to restock their pantry. Sam had taken his laptop to his room and Dean figured it could wait until the next morning.

He lazily stretched and got out of his bed. As he put his robe on, he heard the click of Cas’ door opening.  _ Oh shit _ , he thought.  _ I normally have coffee ready or at least have the machine ready to make a fresh pot.  _

Quickly, he tied his robe and yanked his door open. Cas was already almost to the kitchen as Dean tried to catch up. Hovering in the doorway, he saw Cas lift the pot and peer into it. Then, he opened the top where the grounds were. His head slowly tilted to the side before he reached up to the cabinet where the coffee was kept. 

Dean walked into the kitchen. “Morning sunshine. Everything okay?”

“Dean, there is no coffee,” Cas deadpanned.

“Well, I slept in today and haven’t made a pot yet. I would think you would know how to start a pot yourself by now,” Dean chuckled.

“No, Dean. There is no coffee. None.” Cas yanked the refrigerator door open. “We have three different kinds of beer, but no coffee. We have Chinese takeout and pizza from five days ago, but no coffee.”

“Well,” Dean slowly said. “We were supposed to go to the store yesterday. I didn’t think we were out of coffee but I’ll head out today and get some. That sound good to you?”

Cas turned to glare at Dean. If he still had any grace left, Dean knew he would have been smited on the spot. “No, that doesn’t sound good to me, but it will have to do, I guess.”

“Not a morning person, at all, hmm?” Dean ran his hand through his hair. “I can probably head out now and make a supply run. Would that suit you better, grumpy?”

Some of the furrows on Cas’ forehead smoothed. Before he could say anything, the sound of the bunker door slamming echoed through the kitchen. Sam tromped into the kitchen with a few grocery bags hanging from his left arm. “Hey guys! I got up and realized we didn’t have any coffee so I went ahead and made a supply run.” He tossed a bag of coffee grounds to Dean.

“Oh thank God,” Dean mumbled. “I thought Cas was going to smite me over coffee withdrawals.”

Ten minutes later, Cas was working on his second cup of coffee, a small smile creasing his face.


	4. Day 4 - A Fourth of July Surprise

**Summary for the Chapter:**

> April 4 - Picknicking

Cas shaded his eyes with his hand, glancing around the lakeshore. Glancing at his phone, he double-checked to make sure he was close to where Dean had dropped the pin on Maps. “Where is he?” he grumbled to himself. Dean had promised a fun surprise for the Fourth. Cas didn’t have a problem with being outside; he actually loved being outside, in a hammock with a good book. But every Fourth of July, without fail, they always ended up at some type of party with a bunch of extremely drunk people. Cas hated being in the crush of a bunch of people and could only stand parties for an hour or so before his introverted nature kicked in. 

“Hey, Cas! Over here!” Cas turned to see Dean waving at him from between two trees.

As soon as Cas was within arm’s reach, Dean turned and walked up a path that Cas hadn’t noticed until that moment. 

“This doesn’t look like the way to our normal holiday parties,” Cas commented.

“Well, that would be because it’s not,” Dean called over his shoulder.

Cas abruptly stopped on the trail. “Wait, what?”

Dean laughed and turned to face Cas. “I told you I had a fun surprise. Cas, do you doubt me that much? After knowing you for most of my life, I know how much you hate parties. That would be a torture surprise for you. Don’t be dumb.”

“Oh,” Cas mumbled. “I just…”

“You just assumed. Now hurry up!”

The trail ended at the lake. Before Cas could get a good look, Dean had loped over and covered his eyes. “Hey!” Cas yelped.

“This is part of the surprise dummy,” Dean said. “Now close your eyes and turn to your right. Count to twenty and then open your eyes.”

Cas bit his lip as he followed Dean’s orders. As his eyelashes fluttered open, he saw Dean standing in front of him holding a single rose. Cas’ jaw dropped. The rose was gorgeous: orange in the center and ombreing out to a deep red, almost like a sunset. His eyes flicked up and caught Dean’s, seeing the hope and fear warring inside of them.

“Dean, it’s beautiful,” Cas smiled. Then, he looked beyond Dean and he let out a small gasp. A huge blanket was spread out on the grass under a large oak tree with candles in glass jars flickering softly around it. A wicker picnic basket sat atop it.

“You did all this for me?” Cas asked tentatively. 

“Of course Cas. Now let’s enjoy this feast I slaved over before the show begins.”

The last rays of the sun kissed the edges of the lake as the two feasted on homemade sandwiches, potato salad and popcorn. Dean had even made homemade sangria for Cas because he knew Cas hated the taste of beer. 

“This has been amazing,” Cas groaned. “You’re an amazing cook Dean.”

“I’m not done yet,” Dean crowed. “Dessert!”

“But I’m stuffed,” Cas weakly said in protest. 

“You have to have a little room left. Come on, Cas.” Dean pouted at Cas, giving him the best puppy dog look he could. 

“I guess so,” Cas smiled indulgently at Dean.”Maybe one bite, so make it count.”

“Well, they are bite-sized…” Dean grinned, pulling out a small tupperware container. He handed it to Cas, biting his lip. 

Slowly, Cas lifted the lid. A grin split his face when he saw the chocolate-covered strawberries inside. “Dean, you shouldn’t have.”

“I know I didn’t have to,” Dean softly said. “I wanted to.”

Before Cas could respond, the sound of fireworks filled the air. 

“Hey the show is starting. Come here, Cas.” Dean patted the blanket beside him. “Get comfortable.”

Cas edged closer to Dean. Suddenly, Dean reached out and pulled Cas against him. Cas froze up but then he let Dean’s warmth and the sangria relax him and he leaned deeper into Dean.

“Is this okay, Cas?” Dean murmured into Cas’ hair.

“Why wouldn’t it be?” Cas questioned back.

“I just don’t want you to feel like you’ve been forced into anything. I want you to know how much I l-” Dean froze. 

Dropping the strawberries, Cas turned to face Dean. “Dean, you’re an idiot.”

“Not the reaction I was hoping for,” Dean mumbled, head down.

Cas grabbed Dean’s chin, forcing eye contact. “I love you, you idiot. I was just waiting for you to get your head on straight.”

“Not exactly straight though, is it?” Dean quipped.

“Oh shut up,” Cas playfully shoved Dean. As Dean fell, he pulled Cas with him. The two snuggled on the blanket, watching the display of fireworks play across the summer night sky.

**Notes for the Chapter:**

> Huge shoutout to my bestie for giving me the inspiration for this summer night picnic.


	5. Day 5 - The Perfect Pie

**Summary for the Chapter:**

> April 5 - Baking together

**Notes for the Chapter:**

> I went a little over the 1,000 word max but I just got so caught up in being in Cas' head at the beginning. It was too much fun. Plus, I love Dean being in teacher mode.

Castiel had been on Earth for several years now, as both an angel and a human. He liked to think he had at least a decent understanding of why humans did the things they did. Granted, some had purer motivations than others and every human was different, but they each had the same basic instincts and survival needs.

One of the things humans needed to survive was food. But food wasn’t just something you consumed to keep living. Humans had turned it into so much more. It was an art form, a social outing, a comfort. For some, it was a necessary evil. 

And the wide variety of food. Although Castiel couldn’t really taste food anymore as an angel, he could appreciate the breadth of human inventiveness. And the smells, now those Castiel could still enjoy. There was a certain bakery in Paris that never failed to remind him of Balthazar. The smell of croissants always made him smile, even as his heart ached.

His human family though had a strange relationship with food. The two brothers were at laughably extreme ends of the scale when it came to eating habits. Sam was never happier than when a case brought them to a town with a decent array of healthy food. Castiel knew that Sam liked eating healthy to try to keep himself in the best shape possible and to make up for all the years of bad nutrition he had growing up.

Dean, on the other hand, was an entirely different creature when it came to food. He was almost worshipful in some respects. He could rate most of the diners up and down the roads they traveled and would never turn down bacon. (Castiel had learned that lesson the hard way.)

As much as Dean loved burgers and bacon though, there was one food that had them all beat: Pie. Castiel sat at the map table in the bunker, thinking about pie. He still remembered the fiasco at the gas station when he tried to buy Dean pie. And although Dean would gladly consume any pie, Castiel thought about his research into baked goods and knew that homemade would be best.

There was one problem with homemade pie, though. Castiel had no idea how to go about making a pie.

Of course he had read countless recipes but he was still uncertain. He had no way of tasting the pie to make sure it was edible. Wouldn’t that be a disaster? Giving Dean a pie that wasn’t even fit to eat?

Unconsciously, he buried his head in his hands. He didn’t even realize that anyone else was in the room until he felt a hand on his shoulder. Turning, he saw Sam’s concerned face.

“Are you okay, Cas?” Sam asked.

“I’m okay, Sam. I...well, I wanted to make a pie to give to Dean but I’m a loss of where to start.”

Sam laughed. “Well, that’s easy. Why don’t you ask him to teach you? You know how Dean likes to teach, even if he makes a fuss about it.”

Castiel thought for a second. “That’s a great idea. Thank you, Sam!”

Before he lost his nerve, he quickly walked toward Dean’s room.

“He’s in the garage!” Sam yelled behind him.

As Castiel opened the garage door, he saw Dean working on Baby’s engine, humming happily to himself.

“Dean,” Castiel called out. “I had a favor to ask you.”

Wiping his hands on a rag, Dean turned to Castiel, smiling. “What’s up Cas?”

“Can you teach me how to make a pie?”

Dean’s smile grew wider. “Of course dude! Everyone should know how to make a pie. Any flavor preference?”

“Uh,” Castiel stammered. “Whichever you think is the best flavor.”

“We’ll go with apple. It’s a classic. We should have most of the ingredients but we’ll have to get some apples from the store.”

An hour later, Castiel stood beside Dean, watching as the hunter lined all of the ingredients up on the kitchen counter.

“Okay, first, you want to preheat your oven so that when we’re ready to pop the pie in, the oven will be ready.” 

Dean watched as Castiel turned the oven to the correct temperature.

“Now, we’re going to combine our dry ingredients. Now, nutmeg and cinnamon are regulars but I like to add ginger to my pie. Adds more depth.”

Castiel sifted the ingredients together, then looked at Dean for guidance.

“Slice your apples up thinly. Hold up,” Dean grabbed Castiel’s arm. “Dude, you use an angel blade all the time. I would think you’d be skilled with a knife.”

“Dean, fighting and baking are not the same. What am I doing wrong?” Castiel grumbled.

“Here, watch me.” Dean deftly sliced an apple into even slices. “Now, you try.”

Castiel eyeballed the apple before raising the knife. Before he could even slice into it, Dean slid behind him. “Don’t think about it too much,” Dean softly said. “Like this.” He guided Castiel’s hands, slicing the apple almost perfectly. “Got it now?”

“Yeah, yeah I think so,” Castiel stammered, as he continued slicing apples, not meeting Dean’s eyes.

The lemon juice slid into Castiel’s eyeline. “Add this and then toss the dry mix in with the apples. Make sure they’re all coated.”

When Castiel had put the apples aside, Dean motioned for him to come over to the other counter. “Now roll your crust out, line the pie plate with it and trim off the excess. That’s perfect, Cas.” Dean handed him the apples. “Pour these in and dot some butter on top.”

Castiel scrunched his forehead up as he made sure the apples laid evenly and dotted butter evenly across the pie.

“Now for the fun part. Cover it with more pie crust, crimp the edges and cut some slits in the top. Next time, we can try a lattice crust.”

“Next time?” Castiel asked, glancing at Dean.

“I, I um, mean if you want to keep learning. You don’t have to,” Dean stammered as the tops of his ears turned red.

“I’d like that,” Castiel smiled. “Do we put it in the oven now?”

“Yep for 25 minutes covered, then 25 more uncovered.” As Castiel set a timer, Dean fiddled with the edge of his flannel. Before Castiel could ask what was wrong, Dean blurted out, “Why did you want to learn how to make a pie?”

Castiel felt heat flood his face. “Well, I originally wanted to make you a pie and surprise you with it but I wanted to make sure it was a success. Sam suggested that I should get you to teach me.”

“So, that pie’s for me? You wanted to make me pie?” Dean’s mouth gaped open. “Why?”

“Well, I wanted to show you how much you mean to me. I didn’t think flowers would be appropriate. You love pie, so I knew you would appreciate it.”

“Dude,” Dean beamed at him. “You’re amazing.” He enveloped Cas in a hug. “Don’t ever change.”


	6. Day 6 - Fun Family Outing

**Summary for the Chapter:**

> Day 6 - Ice skating

**Notes for the Chapter:**

> To preface this drabble, I took major liberties with how the series is going to end. This takes place post-series. Sam, Dean, Cas, Jack and Mary are all alive. Chuck came back and restored Jack’s soul and Cas is a full-fledged angel, wings and all. Enjoy! :D

It had been a month since everything had settled back down at the bunker. They had rescued Cas from the Empty, as well as bringing back a host of angels to fix Heaven. Things finally seemed to be normal again, at least as normal as it got for the Winchesters. Without much conscious thought, they hadn’t been actively seeking out cases, instead choosing to stay close to home and recover.

One night as they all sat around the table, Mary piped up, “We should do something fun. Together as a family, ya know?”

“Like what?” Sam asked.

“Nothing major. What’s something none of you have had a chance to do before?” Mary sat up, glancing around at all of the guys. “We should hold off visiting any type of theme park for right now, but something small you’ve always wanted to do.”

“I would like to go ice skating,” Jack stated. “I saw it in a movie that was on last night and it looked fun.”

Mary’s eyes lit up. “I haven’t ice skated in years. What about you boys?”

Simultaneously, Sam and Dean shook their heads. “Cas, what about you?” Mary turned to the angel.

“No, I haven’t had the opportunity,” Cas stated solemnly. “I would like to though.”

“That settles it!” Mary pulled her phone out. “Now we just need to find the nearest rink and pick a day to go.”

Later that week, Dean and Cas took the Impala, while Sam, Mary and Jack all piled into the Mercury Cougar Eliminator that Dean had fixed up for Sam. While they could have all squished into the Impala, Mary and Sam had been giving Dean and Cas space to process where exactly their relationship was going to go. It wasn’t every day that you realized you had been in love with someone for ten years and you used that love to rescue the person from beyond the veil.

As they pulled up to the rink, Jack began bouncing up and down excitedly. Mary’s eyes softened as she glanced back at him, then at Sam and finally at Dean and Cas’ silhouettes in the Impala parked ahead of them. She was so glad they had managed to save Cas and Jack. Their loss would have been devastating.

Shaking her head, she resolved to just enjoy a fun outing with her boys.

Dean grumbled as he laced his skates up. “Why did we decide to do this? I’m going to break my neck.”

Sam snorted. “That’s what the rail on the outside is for.”

Mary laid a hand on his shoulder. “You’ll be fine. I’m sure you’ll pick it up in no time. Plus, all of you haven’t skated before. You can learn together.”

Holding his breath, Dean tentatively stepped onto the ice. His legs shook a little, but he held the rail for support. Mary had glided onto the ice, easy as breathing. Jack was trying to follow her, arms out for balance. Dean turned around and almost fell as he watched Sam step out and immediately slip.

Finally, the only person not on the ice was Cas. “Come on babe,” Dean called out.

Cas tilted his head at the endearment and beamed at Dean. He stepped out and started gliding effortlessly. Dean’s jaw dropped. 

“How are you doing that? Did you lie about skating before? Even Jack’s having problems.” Dean motioned towards Jack, who had grabbed Mary’s hand.

“It’s really not that hard, Dean,” Cas smirked. “Don’t think about it too much.”

_ Okay, wise guy _ , Dean thought. He breathed in deeply and strode out. Immediately, he felt warm arms grab him as he almost face-planted. 

“Thanks Cas,” Dean mumbled into the trenchcoat. As Cas helped him to his feet, Dean felt the faintest whisper by his face. Contemplating for just a second, he pushed Cas backwards.

“Dean!” Mary yelled from across the ice.

Before Cas could fall, Dean felt the whoosh of air again. “I knew it!” Dean crowed. “You’re cheating.”

Mary pulled Jack towards the couple and Sam shakily made his way over. 

“How is he cheating, Dean?” Mary asked, eyebrow raised.

Dean smirked. “Wings.”

Cas’ face flushed. “You didn’t say I couldn’t balance myself however I see fit.”

“Wings aren’t fair babe. Jack isn’t using his. Right, Jack?”

Jack’s eyes widened. “I didn’t know that was an option.”

Dean held up a finger. “That’s because it’s not. No wings, Cas.”

“Fine,” Cas grumbled. He held out a hand out to Dean.  The two started to glide forward and immediately fell into a heap with Cas sprawled across Dean.

“Okay,” Dean grumbled. “Maybe use wings just this once.”


	7. Day 7 - A Binding Promise

**Summary for the Chapter:**

> April 7 - Wedding Day

Dean was an absolute mess. Staring at his reflection in the mirror, he tried, for the fourth time, to tie his tie. Sam chuckled from behind him, nudging Dean’s hands aside and forming a perfect Windsor knot in the green tie. “Nervous, bro?”

Scrubbing a hand through his hair, Dean let out a nervous laugh. “What’s there to be nervous about, Sammy? Not like he’s going to say no.” Freezing in place, he whispered, “What if he says no?”

“Dude, seriously?” Sam shook his head. “He already said yes to your proposal. The two of you have been connected at the hip since you were little. You finally got up the nerve to ask him out in high school. Then you asked him to move in with you. Every time, he’s always said yes to you. Why do you think that’s going to change now?”

“I don’t know man,” Dean turned to look out the window at the preparations happening in the backyard. “I just keep feeling like it’s too good to be true. That it was too easy.”

“Yeah, right. Between your self-esteem issues and Cas’ lack of confidence, I was surprised the two of you even got together. Not for a lack of love for each other but because you were both too thick to realize what was right in front of you. Trust me,” Sam reached out, grabbing Dean’s shoulder and making him turn to face him, “there’s no way that Cas is going to let you go.”

“I know,” Dean sheepishly smiled. “I just..”

Before he could finish, a small knock came from the closed bedroom door. Sam opened the door a crack but didn’t let Dean look out. “What are you doing here, Cas?”

“I know we’re not supposed to see each other but, technically, talking through a door isn’t seeing each other. Sam, can you give us a minute?”

Sam eased out of the door and clapped a hand onto Cas’ shoulder. “He’s all yours.”

“Dean?” Cas softly called out. “Can you hear me?”

“Yeah, Cas, what’s up?” Dean laid a hand on the door.

“I know we’re not supposed to see each before the ceremony and all that traditional stuff you claim to hate, but I wanted to check on you. I know how you like getting in your head. So before you start, just know that I love you and I better see your ass walking towards me in twenty minutes or so help me, I will drag you there myself.”

Dean started laughing and soon, Cas joined in. “This is why you’re perfect for me, Cas. Now go before I decide to break some traditions.”

Twenty minutes later, Dean stood behind an ivy-covered archway. He and Cas had decided to enter from opposite sides and meet in the middle for their ceremony. Cas had gotten the idea after listening to some old country song and wouldn’t budge.

The music swelled and Dean stepped through the lush curtain. His eyes locked onto Cas opposite him. They were both wearing fitted gray suits but, where Dean’s tie was green as a spring forest, Cas’ was the bright blue of summer skies. He felt a smile spread across his face as he winked at Cas.

They met in the middle where Jody Mills, their officiant as well as a longtime family friend, was waiting for them. 

“Good afternoon, all. We are gathered here today to witness the union of Dean Winchester and Castiel Novak in holy matrimony. Today we celebrate, for a married life – a shared life – is a great blessing. As these two embark on their journey together, they will be able to nurture a love that makes them better versions of themselves. Marriage is a garden we sow with love, and harvest in personal growth.

“Dean and Castiel have chosen to write their own vows and it is with these words that you will express your binding promises to love, honor and cherish each other. If you are ready to make these promises, I invite you to face each other and declare your intentions. Dean, when you’re ready, you may begin.”

“Cas, you have seen the absolute darkest parts of my soul. You’ve helped me through more crises than anyone should ever have before the age of 30. You have been an angel to me in so many ways, which I guess makes the devil on your shoulder.” He grinned at Cas as their families and friends chuckled. “But seriously, Cas, when I look into the future, there’s just you. You said once that you didn’t believe in love, that you didn’t think it would happen for you. But you made an exception for me. And I plan on showing you each and every day how much you mean to me. Marriage is hard but there’s no one else I would rather go through the bad times of life with. I love you forever and for always.”

Cas’ face was solemn but Dean could see from the twitch of his eyebrow that he was fighting back tears.

Jody turned to Cas. “Castiel, when you are ready, you may begin your vows.”

“Dean, you are my soulmate in every sense of the word. I would say you complete me but you go beyond that. You make me the best version of myself that I could be. I want to spend the rest of my life with you, not because I love you, because that’s not enough of a  reason to pledge your life to someone. I want to spend forever with you because I don’t know where I end and where you begin. You bring sunshine, light and life to my life. I love you with every particle of my being and I always will.”

Dean didn’t try to wipe away the tears that were streaming down his face. “You had to make me cry, didn’t you?” he laughed. 

“Well you had the market on laughter, my love,” Cas smiled at him.

The two exchanged simple rings and grinned at each other as Jody pronounced them husband and husband.

“I love you, Mr. Winchester,” Cas said.

“Bet I love you more, Mr. Winchester,” Dean grinned as he leaned in to kiss his husband.

**Notes for the Chapter:**

> I drew inspiration for the wedding ceremony from the American Marriage Ministries website where they offer samples of wedding ceremony scripts. I just love the idea of the two of them sharing their own vows instead of the boilerplate vows. I also took some of Cas’ vows from ideas my best friend has on weddings/being with someone forever. Much love, Britt!


	8. April 8: It Should Be Easy, Right?

**Summary for the Chapter:**

> April 8 - Building an IKEA cabinet

“Hey babe, I’m home…” Dean froze in the doorway. “What’s all this?”

Cas looked up from a jumble of wood pieces and metal screws. “Uh, well it’s supposed to be a new TV stand storage thingy to replace our old one.” He waved an instruction sheet in the air. “It was also supposed to be done before you got home, but, well…” 

Dean chuckled. “It’s okay, babe. I’ll have this put together in no time. Let me just get changed first.”

He shook his head as he headed to their bedroom. Cas could bake a flawless cake and take a person down in 5 seconds flat with his kick-ass martial arts skills but hand him a tool bag and he was hopelessly lost. Dean appreciated Cas wanting to surprise him with a completed TV stand. He knew he had been bitching about it relentlessly for weeks now, especially when the shelf with all his games broke in the middle of the night, scaring them both to death.

After changing out of his work clothes, Dean grabbed the directions from Cas’ hand as he settled on the floor beside him. “What even is this, Cas? A Havsta? What language is that?”

Cas rolled his eyes. “It’s the name of the furniture. It’s from IKEA. And I think that’s part 1 of the instructions? I’m not really sure. There were two PDFs on the website so I printed them both.”

Dean studied both sheets. “This shouldn’t be too complicated. Do you have the photo from the website?”

Cas passed Dean his phone. Dean studied the TV stand/bookshelf combination. “Okay, this shouldn’t be too hard, Cas. How long have you been working on it?”

Shifting from side to side, Cas bit his lip. “Uh, maybe a couple hours?”

“Dude, really? Well, we’ll have this together in no time.” Dean wrapped his arm around Cas, pressing a quick kiss to his temple. “Now, hand me the-” Dean froze. “Uh, are none of these pieces labeled?”

Cas turned a board over in his hand. “I don’t think so.”

Dean scrambled to his knees. “No, no. They should be numbered or lettered or something. They always come with little stickers that tell you which piece they are.”

Cas sheepishly smiled at Dean. “There weren’t letters on the instruction diagrams. Maybe IKEA does things differently?”

Scrubbing his face with the palm of his hand, Dean let out a sigh. “Okay, let’s finish sorting the pieces and go from there.”

Two hours later, the base of the TV stand was sitting between the two of them. Cas experimentally poked the side and watched it wobble slightly. Slowly, he brought his gaze up to meet Dean’s, except Dean’s eyes were closed. “Dean, are you okay?” Cas tentatively asked.

A few seconds passed before Dean let out a massive groan. “Cas, I love you. I really, truly do. But I think I kinda want to kill you right now.”

Climbing over the pile of boards they still didn’t know where to put, Cas settled on Dean’s lap, resting his forehead against the blonde’s. “We can still return it. No one has to know.”

Dean’s eyes shot open. “Oh hell no. This is war. I’m building this cabinet or I’ll die trying.”

Cas grinned and extricated himself from Dean’s lap. “Pizza for refueling?”

“Extra cheese!” Dean yelled as he got up and headed to the door.

“Wait,” Cas paused. “Where are you going?”

“Reinforcements,” Dean smirked.

“I don’t even want to know,” Cas shook his head as he dialed their favorite pizza delivery shop.

One hour, one large pizza and several power tools later, Dean and Cas admired their new, improved Havsta unit. “You know,” Cas remarked, “I think this looks better than the original.”

“Hell yeah!” Dean crowed. “Who needs the Swedes’ instructions? This baby is ready for all our movies and games.” He slapped a hand against the side of the cabinet and watched it sway slightly. “On second thought, let’s get some wall anchors before we put the TV up.”

Cas laughed. “Whatever you say, Dean.”

**Notes for the Chapter:**

> As someone who has never built a piece of IKEA furniture, I'm hoping it's easier than the diagrams look. I think I'll stick with my Walmart and Target purchases to be on the safe side.


	9. Day 9 - Saved by the Umbrella

**Summary for the Chapter:**

> April 9 - under an umbrella

“Shit, shit, shit,” Dean mumbled under his breath. He stared out the library window at the rain cascading onto the quad. It was pouring so hard that he could barely see the engineering building in the distance. Biting his lip, he checked the time on his phone again.  _ Less than 20 minutes before I have to give my presentation. That’s fine. That’s good. Maybe the rain will ease up in the next five minutes. It has to, right? _ He fiddled with the edge of his portfolio. Of all the days to not check the weather and to not have an umbrella in the trunk of the Impala. There was no way he could give this presentation soaking wet. Professor Adler was already riding his ass and would definitely mark him down for appearance.

Watching the clock tick down the minutes, Dean made a decision. He grabbed one of the disposable plastic bags the library had for people to put wet umbrellas in and carefully placed the portfolio inside. He might look like a drowned rat but there was no way Adler was going to give him a bad grade for a soggy portfolio. Tucking the package under his arm securely, he placed a hand on the door, getting ready to make a mad dash for it.

Suddenly, a hand grabbed his elbow. Dean jerked around, hitting his other elbow on the doorframe.

“Ouch!” he yelped.

“I’m sorry. I didn’t mean to make you hurt yourself,” a gravelly voice said.

Dean looked up into gorgeous blue eyes. They belonged to an equally gorgeous guy in a dorky trenchcoat who was standing a little too close but honestly, Dean didn’t mind. 

“That’s okay. Can I help you? I’m about to be late for a presentation that’s a good chunk of my final grade.” Dean cursed his luck.

“I was hoping I could help you. You look like you’re dressed for something important but didn’t have an umbrella.” The guy lifted his hand, a black umbrella clutched tightly. “I thought maybe we could share.”

Dean’s eyes widened. “Dude, you’re amazing. I have to go to the engineering building.”

“Sounds good to me. Ready to head out?”

Dean nodded and pushed the door open. The two strode out onto the quad, the guy’s huge black umbrella big enough to protect both of them but not big enough that their elbows didn’t brush occasionally.

As they neared the engineering building, Dean realized they hadn’t spoken again. “So, thank you so much for doing this. You saved my life.” 

“It was no problem. I had to walk this way and you looked really stressed. I’m glad I was able to help.” The guy smiled at Dean, making Dean’s stomach tingle.

Before he could say anything else, he glanced at his phone. “Shit, I’m going to be late!” He yanked the door open and sprinted down the hallway. Sinking into his seat as the clock hit 11, he realized with a sinking feeling that he didn’t even know the cute guy’s name.

“Stupid,” he mumbled to himself.

An hour later, Dean was fairly confident he had earned at least a B on the presentation. Several other people had come into the class soaked and he had watched as Adler had turned his nose up at them.

_ Wish I could buy that guy coffee or lunch as a thank you _ , Dean mused to himself. Shrugging his shoulders, he headed toward the main entrance.

“Damn, it’s still raining buckets,” he grumbled. At least, he could go home and change. Out of the corner of his eye, a huge black umbrella got his attention. Swiveling around, Dean noticed the edge a tan trenchcoat from under the umbrella. Without even thinking, he slammed the door open and took off across the quad.

As he got close, he tried to slow down but only succeeded in sliding into the trenchcoated figure. A pair of startled blue eyes locked onto his. “Hello again,” the guy murmured.

“Hi,” Dean said, a flush staining his cheeks. “I realized after I was in class that I never introduced myself. I’m Dean.”

A gummy smile spread across the guy’s face. “Hello Dean. I’m Castiel.”

Dean grinned. “Well, Castiel, you really saved my ass with your umbrella. I was thinking I could maybe buy you lunch to make it up to you?”

Castiel’s eyes lit up. “I’d like that very much.”


	10. Day 10 - Oh, that's what you meant!

**Summary for the Chapter:**

> April 10 - 1950's version of them

**Notes for the Chapter:**

> There are brief touches of the 1950's throughout this. I didn't add too much slang because I didn't want it to sound like too cheesy.

Dean had been working up the nerve to talk to Castiel for days now. He had every right to be worried, what with the whole McCarthy business happening. Thank God Dean didn’t work for the federal government. His brother, Sam, was an attorney in the Department of Justice and had told him of the investigations. Dean shuddered. Granted, he wasn’t going around waving a rainbow flag but since moving to Los Angeles he had felt a little freer.

Lately, he had been going to a bar called Purgatory. The owner, Benny, always turned a blind eye to any of the milder shenanigans that happened. He also seemed to be pretty open-minded if his decision to kick out any homophobes was any indication. Dean just liked the atmosphere. He never felt like he stuck out; in fact, he blended in pretty well with his flannel shirts and penchant for anything cowboy related. There were plenty of guys who dressed preppy and some who worshipped at the altar of the Hawaiian shirt. The greasers though, they were the ones who drew Dean’s eye week after week, especially Castiel.

He had overheard the other guy’s name when he was passing their group to go to the restroom. The guy was absolutely gorgeous. He wore the same thing almost every week: a white tshirt and dark jeans with his trademark black leather jacket. His hair always had that just-fucked look to it that Dean couldn’t stop staring at. And his eyes! As soon as Dean saw those eyes, he was hooked. Once, he was face-to-face with Castiel at the bar when they were both ordering drinks. Castiel had turned and winked at Dean and Dean felt like he melted to the floor. Before he could collect himself, Castiel had sauntered back to his friends.

Not this week, Dean thought. He was going to say something, anything, to Castiel.

Fiddling with his drink, he snuck a glance at the group just as they started laughing at the antics of one of their friends. Castiel had thrown his head back and Dean could hear his peals of laughter over the music. 

Turning back to his drink, he saw a guy approaching the group of girls beside him. The guy was suave looking, one of the preppy guys who frequented the bar. He walked up to the giggly blonde sitting in the middle of the group, smiled at her and said, “Come on snake, let’s rattle.” She looked at her friends and, giggling, took his hand. The two of them made their way to the dance floor and started moving to Elvis Presley’s ‘All Shook Up.’

Dean gulped the last of his whiskey and turned toward Castiel’s group again. As his eyes moved toward Castiel, the other man caught his eye and winked. Dean felt a flush spread across his face. Before he could get up, the dark-haired man was making his way to the bar.

“Hey, good looking,” Castiel murmured.

Dean opened his mouth, but nothing came out.

Castiel let out a soft laugh. “Speechless, huh? That’s cute.”

Dean’s eyes flicked to the couples on the dance floor then back to Castiel. He cleared his throat, grabbed Castiel’s hand and said, “Come on snake, let’s rattle.”

Dragging Castiel onto the dance floor, Dean didn’t notice how Castiel had locked up at those words. When they were in the middle, he turned to face Castiel only to see a fist as it came crashing into his face.

“What the hell, man?” he spluttered, dabbing at his nose to make sure it wasn’t bleeding.

A cold glint had settled into Castiel’s eyes. “You said you wanted to rattle. You could have just said you didn’t like the attention.”

“I wanted to dance!” Dean yelled. “It’s slang, man. You say it to someone you want to dance with!”

Castiel suddenly started laughing.

“I don’t get what’s so funny. You’ve been winking at me and I finally decided to make a move for you to punch me,” Dean darkly said, starting to walk away.  _ Figures the guy was just fucking around _ , he thought.

A hand grabbed his. “I’m laughing because in my group, if you say let’s rattle, it means you’re ready to fight.” He broke out into a fit of giggles. 

Dean’s eyes widened. “Really?”

Castiel threaded his arm around Dean’s waist. “I would love to dance with you but I think we should get something for your face first.”

“A milkshake would be nice,” Dean murmured, leaning into Castiel’s touch.

Castiel let out a peal of laughter. “Whatever you want cutie, as long as you give me your name and number in payment.”

Dean smiled. “It’s a deal.”

**Notes for the Chapter:**

> I saw a prompt on Pinterest about 1950's slang and thought it was hilarious so I had to use it for this day.


	11. Day 11 - What is Snapchat?

**Summary for the Chapter:**

> April 11 - Silly Snapchat selfies

**Notes for the Chapter:**

> Earlier this month, I forgot to read the entire 30 days list and used Snapchat in Day 1's drabble of a selfie together so I decided to do a college AU. Enjoy!

Dean tapped a pencil against his temple. His physics homework was going to be the death of him. For the hundredth time, he wondered why he was taking these classes. Sammy had always been the brains of the family. Before he could let himself fall down the self-doubt rabbit hole, he heard a stifled laugh from behind him, followed by the snap of a camera.

Turning around, Dean shot his roommate and best friend, Cas, a curious expression. “I know I look like I’m dying, but you don’t have to document it,” he huffed.

Cas startled, looking up at Dean. “Oh, I was snapping Charlie back.”

“Snapping?” Dean’s eyebrow raised.

“Yeah, she made me download Snapchat when we got dinner earlier. She hasn’t harassed you about it yet?”

“Nah,” Dean swiveled around fully in his chair. “I’ve been swamped this week with physics and then this English research paper that’s due at the end of the week. I wouldn’t have even seen you if we didn’t live together.”

“Well, be prepared. It’s pretty fun actually.” Cas’ phone chirped. “She’s just replied. Come here and I’ll show you.” He patted the bed beside him.

Dean grabbed the pillows off his bed and threw them on Cas’ bed to lean on. After he made himself comfortable, Cas leaned towards him. He clicked a little yellow square that had a white ghost on it. The screen changed to a camera showing Cas’ legs under the phone. Cas clicked a white square at the bottom left, which pulled up what looked like a message list. Charlie’s name was one of only a handful on the screen and had a red square beside it.

Cas clicked the square and Charlie’s face filled the screen, with a rainbow pouring out of her mouth.

“What the hell?” Dean laughed. “Is she trying out some new cosplay or a Halloween costume?”

Cas laughed, eyes crinkling. “It’s a filter. Charlie loves them. Here, I’ll show you.”

Cas flipped back to the camera, clicking a button to enter selfie mode. He tapped the screen again, causing a bunch of circles to appear at the bottom. Dean’s eyes widened as Cas scrolled through the options. One gave them both dog ears, another gave them full gray beards and a third had flower crowns on both of their heads. Cas smirked as he quickly took a picture of them with flower crowns. Before Dean could protest, he sent it to Charlie without a caption.

Not even a minute passed before Cas’ phone chirped again. This time, a purple square was beside Charlie’s name. “Oh, she sent a video,” Cas said.

“You can do that too?” Dean asked incredulously.

Cas clicked the square and Charlie’s face filled the screen. Little sparkles surrounded her face and she was squealing. “Oh my gosh, make him do the dog one!”

“Is something wrong with your phone?” Dean asked.

Cas started laughing. “No, some of the filters change your voice.” He switched back to camera mode and found the dog filter. Leaning close to Dean, he smiled. Dean opened his mouth and yelped when a tongue appeared on the screen. Cas started laughing and a tongue rolled out of his mouth on screen. 

“Are you going to take the picture or what, Cas?” Dean knocked into Cas’ shoulder.

“I’ve been taking a video, Dean,” Cas’ shoulders shook with laughter. 

“What the hell, man!” Dean tried to act offended but couldn’t keep a straight face. Cas had already sent the video to Charlie. “We may as well send her some more.”

The two of the leaned back, snapping photos with all of the different filters. Cas busted out laughing when one of the filters turned Dean into a beauty queen. Surreptitiously, Cas hit the save button before sending it to Charlie, knowing she was going to screenshot it.

“What’s that one?” Dean pointed to the last circle.

“Oh, it’s a face swap.” Cas thumbed over to it.

The two of them broke into peals of laughter. “Dude, this is what nightmares are made of,” Dean said between laughs.

“I didn’t think anything could make you unattractive but this takes the cake,” Cas snorted.

Dean side-eyed Cas. “So I’m normally attractive, huh?”

“Oh shut up,” Cas said. “You already know that. I should probably work on my Spanish homework before it gets too late.”

“One more photo!” Dean pouted at Cas, widening his eyes.

Cas sighed. “Fine. Do you want to pick the filter?”

“Uh…” Dean paused, then his eyes lit up. “Do the heart one.”

Cas’ eyes narrowed. “The crown of hearts?”

“Yeah, we hadn’t used that one yet.” Dean’s eyes sparkled with mischief.

“Ooookay,” Cas slowly said, finding the filter.

Cas smiled into the camera and, just as his finger went to hit the shutter, Dean turned and planted a kiss on his cheek.

Cas’ eyes widened. “You should save that one too,” Dean softly laughed.


	12. Day 12 - May I have this dance?

**Summary for the Chapter:**

> April 12 - ballroom dancing

****

Dean straightened his bowtie in the mirror of Sam’s bathroom. He heard his phone chime from the spare bedroom.  _ Probably Cas wondering when I’m going to arrive tonight _ , Dean smirked to himself.

The two of them had been attending the town’s annual masquerade fundraiser for five years now, ever since they had started seeing each other seriously. Usually, they arrived together but this year, Dean wanted to surprise Cas. He had bought a new tux and had given Charlie money to order him a mask. 

Cas had pouted, whined and even tried flirting with Dean to wheedle the reason why Dean was being secretive. Dean had just laughed and told him to learn some patience.

Sam popped his head in the bathroom. “Almost ready?”

“Yeah, yeah,” Dean glanced in the mirror, running a comb through his hair one last time. The two of them piled into the Impala. 

“So, does he suspect anything?” Sam asked, pulling his mask out of an Amazon box.

“He knows something is happening but doesn’t know what. He’s been irritable all week. I’ve never really hid something from him before and it’s driving him insane. I thought for sure he was going to make me sleep on the couch last night.” Dean chuckled, remembering Cas’ crossed arms and stormy eyes. “The man hates surprises.”

“Well, I’m sure he’ll feel differently after tonight,” Sam smiled at Dean as they pulled into the convention center parking lot.

Dean smirked. “We’ll see.”

Sam had finished tying the simple black eye mask on his face as Dean carefully removed the silver filigree mask from the tissue-lined box Charlie had slipped him at work that day. “Do you mind helping me?” he asked Sam, gesturing with the mask.

“That’s amazing, Dean.” Sam carefully tied the silver ribbons behind Dean’s head.

“Well, I wasn’t going halves on tonight, that’s for sure.” Dean pulled his phone out, smiling at Charlie’s text. “They’re here. Charlie texted me, ‘Grumpy has arrived.’”

Sam and Dean slipped through the back entrance of the convention center. As they joined the throngs of people in the main banquet hall, Dean’s eyes swept the room until he spotted Charlie’s brilliant red hair. Beside her was Cas in a wine-colored suit and dark gray mask.

Slowly, he threaded his way through the crowd. As the clock hit 8, the band started playing “I’ll Be” by Edwin McCain. “Can I have this dance?” Dean softly said as he tapped Cas’ shoulder.

Cas whipped around. His eyes widened as he took in Dean’s tux and mask. He placed his hand in Dean’s outstretched one and let himself be led onto the dance floor.

Dean smoothly stepped into a waltz, leading Cas around the dance floor. As Dean flawlessly executed the first few steps, a huge smile spread across Cas’ face and his eyes started sparkling.

“Dean,” Cas softly whispered, as if he didn’t want to break the spell of the music, “when did you learn to dance like this?”

Dean softly smiled. “You know all of those extra hours I’ve been working the past two months?” Cas nodded. “Well, they weren’t for my job. I’ve been taking lessons with Pam after work several times a week.”

Cas’ eyes widened and glistened. “I—”

“Shhh, Cas, just enjoy the dance.” Dean continued to sweep Cas around the floor. As the music crescendoed, Dean let go of Cas. Cas’ eyebrows raised slightly in confusion and then shot up and Dean dropped to a knee in front of him.

“Cas, when you invited me to the masquerade ball five years ago, I’ll be honest: I thought it was super cheesy and that I was going to hate it. But seeing how much you loved it and enjoyed dancing with me? I realized that night I loved you. And I’ve grown to love you more and more every day since. I like to think I’ve learned some things since that day and I wanted to ask, will you dance with me for the rest of our lives?”

Cas yanked him to his feet. “Yes, a thousand times yes!”

The room burst into applause and Cas saw, through his tears, all of their family and friends had gathered around the edge of the dance floor.

“You did all this for me?” he softly whispered to Dean. 

“Well it helped that Ellen was the masquerade organizer this year, but yeah babe. There’s nothing I wouldn’t do for you.” He slid the ring on Cas’ finger as he gently pressed a kiss to his lips.

**Notes for the Chapter:**

> I knew that I wanted the two of them to waltz since it's so romantic so I had to research songs to waltz to. As soon as I saw "I'll Be" on the list, I was sold. I've loved that song since I first heard it in "A Cinderella Story" so of course I had to do a masquerade ball for the boys. And let's be real, Dean secretly loves chick flicks and in an alternate universe would have seen A Cinderella Story. It's iconic.
> 
> And somehow this turned into a proposal. Dean's romantic side just got away from me. :D


	13. Day 13 - Sundays in Bed

**Summary for the Chapter:**

> April 13 - Lazy Sunday morning

**Notes for the Chapter:**

> I typed most of this on my phone so apologies if there are any autocorrect typos!

Cas stretched under the covers, grumbling at the rays of sunlight that were peeking around the curtain.

“We got blackout curtains for a reason, Dean,” he mumbled into the pillow. He waited for the gentle mocking laugh or the warmth of an arm pulling him closer, but nothing came. Rolling over, he cracked an eye open only to see an empty space beside him in bed. “Urgh,” he groaned, burying his face back in the pillow.

“Hey sleepyhead,” a warm voice said from the doorway. Cracking an eye open again, Cas saw Dean leaning against the doorframe, a mug of coffee clutched in his hand.

“That better be for me,” Cas said, still refusing to move. 

“Only if you can sit up for me,” Dean joked.

Rolling his eyes, Cas pulled himself to a sitting position. As Dean neared the bed, Cas held his hands out expectantly. Laughing, Dean handed the coffee off. Cas huddled close to the cup, drinking deeply from it. “Mmm,” he moaned. “This is heaven.”

The bed dipped as Dean settled beside him and raised an arm. Cas nestled in close and Dean’s arm dropped around him, pulling him in even tighter. 

“What do you want to do today, sunshine?” Dean began running his fingers through Cas’ hair. Cas started to almost purr under Dean’s soft touch. 

“Is nothing an acceptable answer?” Cas murmured.

“Lazy Sunday it is,” Dean smiles down at him. “Are you hungry or so you want to stay here?”

“Mmmm,” Cas groaned. “Food would be nice, but that requires effort.”

Dean laughed. “All you have to do is walk to the table. I’ll whip us up some pancakes and bacon.”

Cas nuzzled into Dean’s neck. “This is why I love you.” He placed a line of kisses up Dean’s neck and jawline.

“Keep that up and you won’t get your food, babe,” Dean huffed.

Cas grinned up at Dean through his eyelashes and gently bit his shoulder. “I guess I can stop, if that’s what you really want.”

“I hate you sometimes,” Dean groaned, running a hand through his hair.

“No you don’t,” Cas said before gently kissing Dean. “Breakfast then bed again.”

Thirty minutes later, the two of them curled back up in bed. Cas had somehow intertwined his legs with Dean’s without Dean even realizing it. Reaching for the remote, Dean asked, “What do you want to watch on Netflix babe?”

“Mmm doesn’t matter to me. Nothing too heavy,” Cas mumbled into his chest.

Dean flipped through the options before settling on The Office. They had seen it so many times but it was their favorite for a reason.

Cas has moved his head to Dean’s chest, an ear pressed against him. Dean gently began finger combing Cas’ hair. “What are you thinking?” he asked Cas. 

“Well, I’m not really thinking as much as I’m enjoying,” Cas replied. 

“What?” Dean asked, slightly confused.

Cas turned to face him, blue eyes bright with emotion. “Days like today are my favorite. Just me and you, no plans, no commitments other than each other. I love laying here, just listening to your heartbeat. It makes me feel safe, happy.”

Dean’s heart tightened. Without a thought, he yanked Cas up and kissed him, long and hard. “I love you so damn much,” he whispered, leaning his forehead against Cas’. 

“I love you too, Dean,” Cas softly smiled before leaning in to kiss him again.


	14. Day 14 - A LARP emergency

**Summary for the Chapter:**

> April 14 - Princess and knight

**Notes for the Chapter:**

> I envision this taking place something after season 9. In my mind, Charlie is still alive and Cas still has his wings.
> 
> Also, I went a little over the 1,000 words. Whoops! Once I started writing, I couldn't stop.

“Dean, I need your help.”

Scrubbing a hand through his hair, Dean thought of all the possible things that could be wrong. “What’s wrong Charlie?”

“Well nothing is  _ wrong _ per se, but my social standing is on precarious ground and you could save me. Plus, I think you owe me for something, not sure what though.” He could almost see the pleading puppy dog eyes through the phone.

“I’m sure I do owe you. You need a wing man or something?” He smirked to himself.

“Not quite. Remember how you filled in as my handmaiden a few times?”

“My Queen is requesting her handmaiden’s presence?” Dean’s eyes crinkled in a smile. He would deny it to Sam but he actually loved LARPing with Charlie. It was fun, getting to escape his actual life for a few hours. 

“Well, yes and no. There’s a ceremony this weekend. And no one told me until now,” Charlie let out a heated sigh, “but I need a second-in-command.”

“That’s no issue, Charlie. Just tell me where I need to be.”

“Dean, you’re my bestie, and you love me endlessly, right?”

“Charlie, spill it,” Dean said.

“Your official title will be princess. Please don’t kill me,” Charlie blurted out.

Dean’s head hit the table. “Ughhhh.” He sighed. “Two things. One, you will not tell Sam. Two, I’m not wearing a dress.”

Charlie giggled. “Deal.” After a brief pause she softly said, “One more thing.”

“Oh God, Charlie.”

“You’ll need a knight.” She softly hummed. “Maybe you can ask Cas. He’s got the dreamy, protector thing going on.”

Dean’s eyes widened. Cas? Charlie wanted him to ask Castiel, Angel of the Lord, if he wanted to LARP with them. The one time Dean would be a princess? Before he could respond, Charlie piped up.

“You don’t have to. I can find someone. I just figured you would want to pick someone you wouldn’t mind being around all day. You’ll be side by side from sunup to sundown.”

Dean gulped nervously. “Yeah, Cas would probably be a great idea. I mean, I already know we work well together. I just haven’t explained all of this,” he gestured wildly with hands, knowing Charlie couldn’t see him, “to him yet.”

Charlie laughed. “Well you have a week to get him accustomed to the idea. And I’m sure you can dig up a suitable outfit for him in that time frame. Hell, I’m sure the bunker probably has extra swords somewhere in storage. He doesn’t need a suit of armor. What you wear as my handmaiden would work just as well for him.”

“Sounds good, Charlie. Just text me the details.”

“Later bitches!” she chirped before hanging up.

_ What the hell have I gotten myself into? _ Dean wondered, contemplating how he was going to ask Cas to be his knight, let alone explain the whole LARPing concept to him. Before he lost his nerve, he shot a quick text off to Cas.

**Dean:** Hey, do you have some time to hang out? Been awhile since you were here.

He sat his phone down and went to the kitchen to grab a beer. As he opened the fridge door, he heard the whoosh of wings.

“Hello, Dean,” a gruff voice said behind him.

“Heya, Cas. Long time, no see,” Dean said nonchalantly, taking a swig of his beer. 

“My apologies Dean. Getting heaven back in order after Metatron’s destruction has been time-consuming. I’ll try to make sure I swing by more often.”

“It’s all good, Cas, no worries. I actually had a suggestion of something we could do that wasn’t case-related if you were cool with you. You don’t have to say yes, it’s cool if you’re not into it, but Charlie wanted me to ask and it makes sense…” Dean’s mouth snapped shut as he realized he was rambling.

Cas cocked his head to the side. “Is everything okay, Dean?”

“Yeah, buddy, yeah it’s all good. So, uhm, have you heard Charlie mention anything about LARPing?”  _ Please say yes, for the love of God, please say yes _ , Dean thought.

“Isn’t that role-playing? She’s a queen, correct?” Cas asked.

“Exactly!” Dean beamed.

“And you’re her handmaiden?” Cas interjected.

Dean’s face flushed. “Yeah, that’s right. But that’s the thing. She needs me to step up in leadership with her for a ceremony next weekend and I kind of need an escort. She suggested you might like it. We would be spending all day together. I get it if you’re busy or something though.”

Cas’ eyes sparkled. “That does sound like fun. But what kind of promotion does a handmaiden get?”

Dean scuffed his boot along the floor, avoiding Cas’ eyes. “Princess,” he mumbled.

“And every princess needs a knight, don’t they?” Cas asked.

Dean’s head shot up. “How did you—?” He narrowed his eyes. “Charlie already called you, didn’t she?”

Cas stifled a laugh. “She may have. She also may have said she didn’t have faith that you would follow through. It does sound like fun, though.” Cas’ eyes narrowed slightly, as he gazed past Dean’s face. “I may be able to get my hands on some authentic chainmail, as well.”

“That would be awesome,” Dean breathed, his earlier embarrassment forgotten.

“It’s a plan,” Cas smiled at him.

❇❇❇❇

The next Saturday, Cas and Dean pulled up to a huge field in the Impala. Dean glanced over at Cas, a small smile tugging at his lips. They had spent the night in a nearby motel and gotten dressed before leaving for the day. Dean wasn’t going to lie: Cas looked damn good in the leather armor and chainmail he was wearing. As they got out of the car, Cas looked him up and down.

“See something ya like, Cas?” Dean joked.

Cas squinted his eyes at Dean. “More like something’s missing.”

“Whaddaya mean?” Dean wrinkled his eyebrows at Cas. “Charlie said my normal handmaiden attire would be fine for today.”

Cas smiled at him. “Well, I think you should have something a little extra.” He pulled a small leather bag from the glove compartment. Walking over to Dean, he undid the drawstring and pulled a metal circlet out. He held it out to Dean.

Dean tentatively took the circlet. It was several different strands of white and yellow gold, twining together like vines. He turned it over and over in his hands before glancing up at Cas.

“This for me?” he shyly asked.

“Every royal needs a crown. I saw this and thought it was appropriate. Simple, yet not.” Cas gently took the circlet back and placed it on Dean’s head. “Now you’re ready,” he smirked at Dean, “princess.”


	15. Day 15 - Movies under the stars

**Summary for the Chapter:**

> April 15 - Movie night

Dean glanced over the grassy hillside quickly. He only had about 15 minutes to make sure everything was perfect. Satisfied, he loped back to the bunker garage. Slowing his steps, he carefully made his way down the hall, listening carefully for any footsteps. Peeking into the Dean Cave and seeing it empty, he hurried inside, leaving an envelope perched in the recliner Cas typically used.

Making his way to the kitchen, he grabbed the six-pack of beer and movie snacks he had prepped earlier that day. As he checked his watch, he heard the bunker door swing open. Stealthily, he slipped into the garage and headed outside.

Seven minutes later, Dean heard the soft rustle of footsteps in the tall grass. Looking up from his phone, he saw Cas standing a few feet away, eyes taking in the scene before him. Dean smiled as Cas’ eyes scanned the sheet hung between two wooden poles, the inflatable kiddie pool filled with blankets and pillows, the two small tables holding a projector and movie snacks.

“Hey buddy, I thought we could switch up movie night if you don’t mind,” Dean said.

Cas’ gaze snapped to Dean’s face. “Dean, this is—” he paused, trying to find the words. “This is awesome.”

Dean’s eyes crinkled at Cas’ word choice. “It’s been so nice outside lately that I wanted to try doing a movie night outside.” Dean patted the space beside him in the kiddie pool. “Come in and get comfortable.”

Cas gingerly climbed into the pool. “Aren’t these normally filled with water?”

Dean laughed. “Yeah, it’s a kiddie pool. But I saw online where someone said this was a great da—” Dean froze, realizing he almost called their weekly movie night a date. He faked a cough. “They said it was a great way to enjoy a movie.”

Cas titled his head to the side, confused by Dean’s pause. “Dean, are you sick? We shouldn’t be outside if you are.”

Dean fidgeted slightly. “Nah man, I just got a little choked up. Probably just need something to drink. Hand me one of those beers, would ya?”

Cas took two beers from the pack, handing one to Dean. As he popped the top off, Dean settled back against the nest of pillows he had made. “So tonight, I figured we could watch one of the classics. I know I already introduced you to Stars Wars but one of Harrison Ford’s best roles was in this beauty and its sequels.”

He hit play and watched as the familiar opening scene to Raiders of the Lost Ark played across the sheet. This really was a great idea, almost like they were at a drive-in theater or something. He smiled, filing the idea away for the future.

“Dean,” Cas whispered part way through the movie, “this movie isn’t factually accurate.”

“Shh, Cas, it’s creative liberty. Just enjoy it for the action.” Dean smirked as he watched Cas’ forehead scrunch up.

“Well Indiana is fairly attractive, so that’s a plus,” Cas stated.

Dean choked on his sip of beer. “What?”

Cas turned to look at him, expression open and curious. “That’s one of the reasons you loved this movie, isn’t it?”

“Uh, well,” Dean stammered. “It’s just a good movie.”

“Hmm, okay,” Cas said, turning back to the movie. He scooted further into the pillows and a little closer to Dean. 

Dean’s heart started thumping harder in his chest.  _ How the hell did Cas pick up on his attraction to Harrison Ford? Was he that obvious? _

He sat straight-backed for a few moments before Cas reached out and pulled Dean closer to him. “I thought the point of watching a movie was to relax, Dean,” Cas murmured.

“Uh, yeah,” Dean said. “Sorry, I just got distracted.”

Cas turned to him. “It’s okay, Dean. As is your appreciation of Harrison Ford and Dr. Sexy.”

“Well, okay then,” Dean mumbled. Cas slid over until he was leaning against Dean.

“This was definitely a good date idea,” Cas softly whispered.

Dean felt his face turn red, but he lifted an arm and put it around Cas. “Yeah, I guess it was, Cas.”


	16. Day 16 - Sam's evil plan

**Summary for the Chapter:**

> April 16 - Clothes swap

“Sam, there is no way that I can appear in public like this.” Cas gestured to his blood splattered trench coat and pants. “I could maybe still wear the shirt but I don’t think that would be appropriate.”

Sam frowned. “Can’t you just grace clean your clothes? That’s what you normally do.”

“I would, but my grace is too low at the moment,” Cas softly said. “I can just stay in the room while you and Dean get dinner. If you wouldn’t mind bringing me back a burger, I can continue researching the case.”

“No man, we’re not going to do that to you.” An idea began forming in Sam’s mind. “Look, Dean won’t be back for about 20 minutes. How about you take a shower and I’ll have a change of clothes waiting on the sink for you? Later tonight, we can stop by a laundromat and clean your clothes. We can also stop by a Walmart and grab some changes of clothes for you until your grace issue gets resolved.”

Cas smiled at Sam. “That would be great, Sam. Thank you.”

Sam felt momentarily guilty. “It’s no big deal Cas. You’re family. We look after family.” He pushed Cas towards the bathroom. “There should be shampoo and soap in the shower already. Use whatever you want. I’ll grab some clothes and have them waiting for you.”

As soon as he heard the shower start running, Sam grabbed Dean’s duffel. He had noticed the tension between Dean and Cas had been ramping up, especially since Cas appeared to be falling. It wasn’t just worry though. If Sam had a dollar for every minute they stared at each other, he wouldn’t need to commit credit card fraud to get by.

He smirked to himself. The only good thing about spending so much time with his brother was that he knew Dean all too well. Seeing Cas in his clothes would be like kryptonite to Dean. He ruffled through the bag until he found Dean’s favorite black Led Zeppelin shirt and the pink, blue and purple flannel he seemed to love wearing lately. He pulled a clean pair of jeans and black boxer briefs out too and piled all of the items on the bathroom counter. “Clothes are on the counter, Cas.”

“Okay, Sam. Thank you.”

As he entered the main part of the room, he heard the roar of the Impala pulling up. Quickly he sat at the table, angling his chair and laptop so he had a perfect view of the room. He had just managed to pull up a couple tabs of research when Dean opened the door.

“Ready to go get some grub, Sammy?”

“Uh, sure. Cas is going to join us, too. He’s in the shower right now but he should be out in a few.” Sam acted as normal as possible.

“Oh, really? That’s cool.” Sam smirked at the feigned nonchalance in Dean’s voice. He was so freaking obvious. Distantly, Sam heard the sound of the shower shutting off.

“Yeah, he said he was hungry. His grace is still running low so he had to clean up the old-fashioned way.” Sam glanced up to see Dean fiddling with the edge of Cas’ trenchcoat.

Before Dean could reply, Cas stepped into the main room. Dean sucked in a deep breath. Sam watched as Dean’s eyes raked up and down Cas’ frame, taking in the flannel and messy, mostly wet-hair.

“Hello, Dean,” Cas said. “Sam gave me some of your clothes to wear until mine can get cleaned. I hope that was okay.”

Dean’s eyes continued to roam across Cas. He seemed to linger on the way the jeans clung to Cas’ thighs and the way Cas had rolled up the sleeves of the flannel. Cas stared back at Dean. “If it’s not okay, Dean, I can change back and stay here.”

“What?” Dean blurted out. “No, it’s fine. More than fine. I was just surprised is all. I’m just used to the trenchcoat so it was like bam.”

Cas tilted his head to the side. “I’m not sure what you mean.”

Sam wanted to slam his head onto the table. He should have realized Cas would be too oblivious to pick up on Dean’s obvious attraction.

“Well,” Dean slowly said. “It’d be like if I showed up in the trenchcoat for instance. It would be a shock, ya know?”

Cas looked at Dean blankly. “You can wear the trenchcoat if you would like Dean. It’s not very clean right now though.”

“I just,” Dean raked his hand through his hair. “Just never mind.”

Sam couldn’t take it anymore. “You know Cas, we can just stop and get you some more clothes before we get food. You can change in the bathroom. That way Dean can get his clothes back.” He turned to look at Dean. “I didn’t realize it was going to bother you Dean. My bad.”

Dean froze. “No!”

Both Cas and Sam stared at Dean. “I mean,” Dean stammered, “it’s okay if you want to keep wearing that. It looks good on you.”

Cas flushed. “Thank you Dean,” he softly said.

Sam felt like cheering.  _ Progress _ , he thought.  _ Small progress but maybe one day we’ll get there _ .

**Notes for the Chapter:**

> I love Shipper Sam because I feel like Sam would definitely work to get his brother and Cas together.
> 
> I didn't do a complete clothes swap but I just had the idea of Dean being surprised by Cas wearing his clothes and I couldn't get it out of my head.


	17. Day 17 - An Accidental Kiss

**Summary for the Chapter:**

> April 17 - first kiss

**Notes for the Chapter:**

> This should have gone up long before now. I was supposed to catch up on prompts this past week since I was on a week's vacation before starting a new job but between getting sick and spending the weekend at a friend's house to watch Avengers: Endgame, I haven't written in several days. I promise I'm not giving up on these 30 days, even though they won't be done until sometime in May. Thank you to those who've stuck around reading and enjoy a cheesy first kiss story! :D

Dean looked over at Cas, who was sound asleep next to him. They had been watching Fight Club, Dean’s choice for their weekly Friday night movie night. Ever since they bonded over their love of Stars Wars and Harry Potter, they made roomie movie night a weekly tradition. They traded off who chose the movie, as well as who provided the snacks.

This week had been rough with midterms so Dean didn’t really blame Cas for passing out. Plus, Fight Club wasn’t really Cas’ cup of tea, but Dean had taken it upon himself to educate Cas on the classics. In turn, Cas had been making Dean watch as many rom coms as he was able to find on Netflix and in their campus’ Redbox. As they got closer and watched more movies together, they had migrated from watching from separate beds to the floor to sharing each other’s bed.

Dean felt a small smile tugging at his lips as he watched Cas snooze. His eyelashes gently fluttered as he shifted closer to Dean. He was dying to just pull Cas close to him and snuggle together. Over the past few weeks, he had noticed himself paying more and more attention to Cas: the way he tapped his pencil against his ear when he was reading, how his eyes crinkled almost completely shut when he really laughed, the way he devoted all of his attention to whoever he was talking to.

Charlie was the one who called him out on it. Dean knew he was attracted to guys and girls. He had come out in high school and it was no big deal. But he had never been in a long-term relationship. Something about putting all of your hope and trust in another person was terrifying. Plus, he had seen how losing Mary had absolutely destroyed John. He never wanted to experience that.

All of that was irrelevant when Charlie cornered him after their shared English class. “Spill it, Winchester,” she said, knocking into him.

“What, Bradbury?” he asked, hip-checking her.

“You know what! Who’s the lucky lady or gentledude?” A mischievous smirk played across her face. “You were doodling hearts and bees on your notes all day. Wait,” she paused. “Have you finally admitted to Cas you like him?!”

“What!” Dean almost yelled. “Charlie, I don’t...I mean...what are you talking about?”

“Dude, you’re so far gone on Cas that it’s unbelievable.” Charlie laughed, but stopped when she saw the deer in the headlights look on Dean’s face. “Dean, are you okay?”

“Is it that obvious?” Dean softly said.

“Well, to me it is. I think he likes you too, you know. If the long stares and personal space issues are any indication. The worst he can say is no.”

“Yeah, I guess you’re right,” Dean said, more to himself than Charlie.

Dean thumped his head softly against the wall as he thought about that conversation. It had been two weeks ago and he hadn’t gotten any closer to talking to Cas. He had noticed little signs that maybe Cas was into him but he always shrugged them off as reading too much into the situation.

Cas’ soft dark hair tickled Dean’s cheek as he wormed closer to Dean in his sleep.

Dean glanced up at the TV as Edward Norton’s character realizes that Tyler Durden is actually him. He felt a surge of courage and leaned down to give Cas a quick kiss on the cheek. Friends could kiss on the cheek, too, right? It was innocent.

Just as his lips were about to land on Cas’ cheek, Cas turned and Dean was kissing him, actually kissing him, on the mouth. With a small gasp, he pulled back only to notice Cas’ large blue eyes staring up at him.

“Oh fuck, Cas, I’m so sorry, I didn’t mean to actually kiss you. I’m such an ass, I understand if you don’t want to talk again,” Dean blabbered, panic filling his chest.

Before he could say anything else, Cas had leaned up, grabbing the back of Dean’s head and pulling him in for another kiss. Dean froze, then melted into the kiss, knotting his fingers in Cas’ hair, pulling him in closer.

Cas gently pulled away, resting his forehead against Dean’s. “You worry too much, Dean.” A smile spread across his face. “And our first kiss took entirely too long to get to.”

“I agree,” Dean smiled before pulling Cas in for another long kiss.


	18. Day 18 - Where I Belong

**Summary for the Chapter:**

> April 18 - something sad

**Notes for the Chapter:**

> I'm so sorry :'(

Castiel had been running for days now. After he and Dean had been whisked into Purgatory, he disappeared as quickly as possible. The pained expression on Dean’s face broke his heart but the thought of Leviathans catching up to them and killing Dean? Castiel’s heart clenched at the thought. 

Everything about Purgatory screamed “Run” to him. The oppressive atmosphere, the lack of clear sunlight, the silence...the silence is what got to him most of all. He had been cut off from angel radio before but those times, he hadn’t been an angel. The lack of chatter made him feel adrift and truly solidified the fact that he was alone here. 

Though that wasn’t quite true. He was still bound to Dean and could feel a tentative thread connecting him to his chosen human. But he tried to shut it out as much as possible. Having to always run and hide and sometimes fight was hard enough but having to ignore Dean’s prayers, his pleas for Cas? Not even Alastair could have invented a more perfect torture.

_ You’re doing this for him _ , Cas chanted to himself.  _ Running is protecting him. Leviathans won’t care as much about one human as they do you. You’re not only an angel, but you’re the one instrumental in their rise and fall. They want you dead and Dean  _ _ cannot _ _ be anywhere near you _ . The refrain helped but it wasn’t enough.

•••

Castiel was torn. Part of him was overjoyed at seeing Dean again. The pure light shining from Dean’s soul when he hugged Cas at the riverbank was beautiful. But love and happiness had no place in Purgatory. When they had stopped for one of their infrequent breaks (Dean was only human after all), Benny had cornered Cas.

“How dangerous are you?” He demanded of Cas.

“It would be better if the two of you left me now. You’d be safer,” Cas bit out. It was the truth but, for the love of his Father, he didn’t want to be separated from Dean again.

Benny just chuckled darkly. “You try telling him that he has to leave you. You didn’t see him on the way here. Barely spoke except for when we found a monster and then it was only ‘Where’s the angel?’ I think most things in here are more scared of him than each other now.”

Cas looked over at Dean, unable to hide the affection in his eyes. “He is quite formidable. But,” he turned back to Benny, “when we get to the portal, he has to leave, no matter what. I don’t know if it works for me, but he  has to get out.”

“Well, brother,” Benny drawled. “You better have some excuses and tricks up your sleeve.”

•••

There were so many of them. The Leviathan has found them, just as they reached the portal. Dean had scrambled to the top and was reaching out for Cas, yelling for him to come on. Cas followed him up the side, knowing Dean was too stubborn to refuse. Cas latched onto Dean’s arm until Dean was fully in the portal and then...then he pushed him away. The look on Dean’s face as their hands parted cut Cas. The confusion and heartbreak clouded Dean’s soul and Cas closed his eyes as Dean disappeared.

This had the plan all along: Get Dean to the portal, make sure he made it safely out and stay in Purgatory as penance for all the destruction he had caused on Earth and in Heaven. He had wanted to clue Dean into the plan but after talking to Benny and seeing Dean’s absolute hope at the two of them getting out? He knew there was no way Dean would accept his decision. 

Cas took a shuddering breath before turning to look back at Purgatory. He belonged here. This was where monsters came from and, after everything he had done, wasn’t he a monster? He had almost destroyed everything countless times and for what? And now this. After seeing the utter heartbreak in Dean’s eyes, there was no doubt in Cas’ mind that he was a monster. A tear slipped down his face as he prepared to continue the fight of his life.


	19. Day 19 - Play to Clean

**Summary for the Chapter:**

> April 19 - Gaming together

“Cas, how many times do I have to ask you to not leave all your shit lying around? Our apartment isn’t but so big.” Dean surveyed the cluttered mess before him. Two jackets were piled on the couch, papers were strewn across the coffee table and several pairs of shoes were haphazardly tossed about the room. There were also several water glasses and a plate or two stacked on end tables. Dean pinched the bridge of his nose, trying to keep his cool. He and Cas had first shared a dorm room, then an apartment as they grew closer and closer and their relationship blossomed. He loved living with his boyfriend, except for when said boyfriend felt creativity strike him and failed to clean up after himself.

Cas stumbled into the living room, eyes bleary from lack of sleep. “Sorry honeybee. I just had a major breakthrough and I’ve been writing most of the night. I just fell asleep about three hours ago.”

Dean’s frustration melted away as he gazed at Cas. It was hard to stay mad at him when he was like this, sleepy and soft. “How about this? Beat me in Mario Kart and I’ll forget about the mess.”

Cas’ brow furrowed. “What if you win?”

“Well,” Dean smirked, “you’ll have cleaning duties for the next two weeks. And I mean all of the cleaning duties.”

“Dean!” Cas raked his hand through his hair. “This isn’t fair, you know. You’ve had hours and hours of practice.”

Dean walked over to Cas, pulling the dark-haired man into his arms. “Mario Kart is easy, baby. Anyone can play it. Or are you chicken?”

Cas shoved Dean back with a growl. “Stop trying to bait me, assbutt. I’ll play. And I’ll wipe that smile off your face when I dust you.”

Dean chuckled as he hurried to the console. “We’ll see.”

◆◆◆

“What the hell, Cas?” Dean yelled, sitting on the edge of his seat.

Cas didn’t reply, but a small smirk crossed his face. He bit his lip in concentration, remembering everything Charlie had coached on him. As Peach crossed the finish line on her motorbike, Cas leapt up. “Ha!” he laughed, turning to face Dean.

Dean’s mouth gaped in surprise. “How did you?” Determination set his eyebrows. “Oh no baby, we’re doing best out of three. You’ve been holding back on me.”

The two of them settled on the edge of the couch with only the soundtrack of the game filling the air. Dean whooped as he claimed victory in the second race.

“That was your favorite track, Dean, don’t think I didn’t know that,” Cas remarked, staying as disinterested as possible.

“Well,” Dean laughed, gently tapping Cas’ nose in affection, “how about we both select random this time. That way no one will have a chosen advantage.”

Cas screwed his eyes up, mulling it over. “Fine,” he finally conceded. “But this will decide the winner. No ‘best out of five’ or seven or whatever. Deal?”

“Of course baby,” Dean smiled. He was used to beating Sam and Benny in Mario Kart. Cas had surprised him at first but that’s because he wasn’t giving it his all.

They both groaned as random chance selected Music Park.

“I hate this track,” Dean growled. “Stupid giant music note.”

Cas grumbled his assent.

As the race progressed, they stayed neck and neck. Dean edged ahead a little and got a green shell, which he promptly held behind himself.

Cas drove through the box, getting three mushrooms. He used one to get as close to Dean as possible without hitting the shell. A smile pulled at his lips as he remembered Charlie’s coaching. Entering the final turn, he sharply veered to the right, bouncing off a drum and utilizing his last two mushrooms. As he crossed the finish line in first place, he threw his hands in the air, sinking back into the couch with a pleased smile on his face.

Dean dropped the controller. “How did you know to do that? What the fuck, Cas?”

Cas just smiled. “I think you have a mess to clean up Dean,” he said as he closed his eyes for a much-needed nap.

**Notes for the Chapter:**

> I love my snarky Cas :*
> 
> Also, follow me on [Twitter](https://twitter.com/krislmart) if you want to talk Destiel, Supernatural or any other fandom or if you just want to yell at me if I slack off on posting lol!


	20. Day 20 - Charlie Always Has A Plan

**Summary for the Chapter:**

> April 20 - Pocky game

“This is getting ridiculous.”

Sam jumped, not expecting anyone else to be in the kitchen this early. “Jeez, Charlie, just scare me to death next time, why don’t you?”

Charlie scoffed. “You’re a hunter. You’re supposed to have freaky good instincts. Not my fault you’re off your game Winchester.”

Sam rolled his eyes, but pulled a second coffee mug out of the cabinet. “Enlighten me. What’s ridiculous?”

Charlie jerked a thumb behind her, towards the bedrooms. “Those two. They’re more obvious than the Vegas strip. How have they not realized they like each other yet?”

Sam slumped forward and rested his forehead against the cabinet as the coffee brewed. “Charlie, if I knew the answer to that, I wouldn’t have been living with all the tension for years now.” He closed his eyes, contemplating the situation.

“Well, have you tried?” 

Sam spun around to face the redhead. “Really Charlie?” At her slightly wide eyes, he lowered his voice. No need to wake Dean and Cas up any earlier. “You know how Dean is. Put an emotion in his face and he’ll run as fast as he can in the opposite direction.”

Silence descended over the kitchen as Sam watched the coffee brew. Suddenly, a devious chuckle broke out.

“The answer is obvious, Sam. We have to make Dean think it’s his idea.”

A few days passed with no further comment from Charlie but Sam knew better than to think she had forgotten. He was proven right when at breakfast Charlie made an announcement.

“We should have play drinking games tonight.”

“Drinking games?” Cas asked, raising an eyebrow.

“Yeah,” Charlie beamed. “Or just games while we drink. Let’s let loose and have some fun tonight.” She looked between Sam and Dean and started pouting. “Please?”

Dean sighed. “Why not? We deserve a night to just kick back.”

“Sure,” Sam said, making sure to hide the smile he was fighting. He was dying to know what Charlie had up her sleeve.

Before he could corner her for details, she flew out the door, yelling about a supply run. Sam shook his head and got ready for a morning run.

That night, they had already played a few rounds of beer pong and a rousing game of Kings. They were all pretty loose and relaxed. Sam had bit back a smile when he saw Dean and Cas continue to invade each other’s personal space. Charlie had gotten up to get more drinks and when she came back, she held up a slim box.

“What’s that?” Dean asked.

“I picked up a box of pocky when I was in the store.” Charlie sat the box down nonchalantly as she distributed drinks. Then, she let out a little gasp. “We should play the pocky game! It was so much fun in school.”

“Pocky game?” Sam questioned.

“Yeah!” Charlie gushed. “Two people face off. Each person puts one end of the pocky stick in their mouth. You keep biting forward. The goal is to reach the middle first without drawing back. Brings out the competitive streak in some and the chicken in others,” she laughed.

Cas’ eyebrows were drawn together. “How do we decide who plays?”

Charlie tapped her finger against her chin. “How about we flip for it?”

A few coin flips later, Dean and Cas faced off against each other. Sam made a mental note to ask Charlie if she had figured out how to weight a coin because no one was that lucky. The two men looked at each other as they got in position. 

“Ready?” Charlie asked. They both grunted their assent. “On your mark, get set, go!”

They both bit forward and, as they neared the middle, Sam noticed the tension in Dean’s body. He would start to slow but then noticed how Cas would speed up. It was neck and neck and then…

Charlie squealed. Loudly. Sam half thought about glaring at her mockingly but he was too happy for his brother and one of his best friends.

Dean had reached the middle first and, after a millisecond of hesitation, he kept going and kissed Cas. Cas froze but immediately melted into Dean, reaching his hands up into Dean’s hair. Dean’s arms snaked around Cas’ back, pulling him tight. They continued kissing, oblivious to Charlie and Sam’s presence. 

Sam reached out and grabbed Charlie’s arm, slowly and silently pulling her away.  _ Thank God _ , he thought to himself.  _ It’s about time. _

**Notes for the Chapter:**

> I love Shipper Sam and Shipper Charlie.
> 
> Let's be real, I just love Charlie no matter what. She's such a fun character to write!


	21. Day 21 - Two Swords

**Summary for the Chapter:**

> Day 21 - They fight/argue

**Notes for the Chapter:**

> I didn't really want to write an argument so I took a little creative liberty with the "they fight" trope and it got away from me a bit.

Dean Winchester, captain of the Impala, swaggered into Havana’s main marketplace. He had just put his ship into harbor and was ready to get to Ellen’s tavern and let loose after the long journey. The agents of the East India Trading Company had become ruthless as of late. This past trip had been a narrow escape before he could rid himself of them.

Too late, he noticed a hush had descended over the courtyard. His eyes flicked up and caught a flash of brilliant blue that had his hand reaching for his sword.

“Novak,” he called, barely holding back a laugh. “How did I get so lucky to make port the same time as you?”

“Maybe it wasn’t luck, Winchester,” Castiel growled low in his throat. He walked across the courtyard lightly, with catlike grace. His dark brown coat was pushed back, revealing the blue waistcoat that had become his trademark. “Did you think that I would forget? I remember Port Royal very well, thank you.”

Dean sidestepped, drawing his blade. “Of course you remember. Well, on with it then.”

Castiel’s sword was in his hand before Dean could take another breath. One blink and Castiel was lunging forward, blade aiming for Dean’s throat.

Dean parried Castiel’s blade. “You’re getting slow Novak,” he laughed.

Castiel spun to the right, blade flashing in the light. “Then what are you Winchester?”

Dean’s left hand reached across his body, trying but to no avail. He ducked backwards, narrowly avoiding getting his head lopped off.  _ Damn Castiel _ , he thought, giving up on trying to reach his pistol for now.  _ Not that I would use it. Probably. _

Beads of sweat ran down his face and he blinked the salty drops out of his eyes. He might not be seeking the killing blow but Novak wasn’t a different story.

The two men continued to whirl about, blades flashing silver in the light. Then, suddenly, they heard a growing cacophony of noise. Their eyes locked and, with a short nod each, they turned towards the noise. 

“Shite,” Dean cursed. Several members of the East India Trading Company were flooding into the area. Out of the corner of his eye, he saw Castiel straighten, tension setting in his shoulders and spine. 

“Take a pause on killing me mate until we both get out of this?” Dean said in a low voice to Castiel. Castiel nodded curtly, taking a defensive stance beside Dean.

Dean shifted, mimicking Castiel’s stance. Seven men were in the courtyard but Dean wasn’t foolish enough to believe that more were not coming. But, if he and Castiel could get by these seven, they stood a chance at escape.

They easily dispatched the first two. The Company’s men were well-trained, that was for sure, but they were no match for the hours of dedication Dean had put into swordplay. Still, five men against two wasn’t a battle easily won. Dean found himself back to back with Castiel, both easily parrying enemy blows. 

“Duck!” Castiel yelled, and Dean dropped without question. He felt the whoosh of steel above his head. He rolled out of the way of the other man’s blade and easily dispatched him. As he turned around, he saw Castiel disarm the last man. Before either man could say a word, they heard the distant shouts of a large group of men. 

Dean spun and readied himself to run but Castiel grabbed his elbow. “Together or not at all,” Castiel softly said. 

Dean’s brow wrinkled. “Why should I trust you?”

Castiel smirked at him. “I never said you should trust me. But I think we proved today that two swords are better than one.”

“And what? You’ll make an exception for me?” Dean scoffed. 

“We can make it up as we go,” Castiel stated.

Dean shook his head. “I’m probably a fool for this, but I’ll do it anyways. Let’s go before we really have to fight our way out.”

Castiel smiled at him, truly smiled, and Dean knew he was sunk.  _ What the hell _ , he thought.  _ I always was lured in by a pair of blue eyes. _

The two raced for the safety of the Impala.


	22. Day 22 - Baby Needs A Bath

**Summary for the Chapter:**

> April 22 - water fight

Suds formed across the surface of the Impala. Dean sighed in contentment, dunking the sponge into the bucket. This was one of his favorite things to do. Sam knew not to bother Dean when Dean went into the garage to wash Baby. He would take at least an hour a week to thoroughly wash her exterior and detail the interior. It was therapeutic in a way.

He hummed along to the music before singing along to Led Zeppelin. The music distracted him so much that he didn’t hear the sound of the door opening. He smiled as he truly got into the music, hips swaying slightly as he reached across Baby’s hood. As the music swelled, he spun around only to be met with Cas’ sparkling eyes and twitching mouth.

“Shit, Cas!” Dean yelped, dropping the sponge on the floor. “Let someone know when you’re in the room instead of giving them a heart attack.”

Cas’ mouth twitched some more before he let out a sharp laugh. “I thought you would have heard the door open. And you were enjoying yourself so much that I felt it would have been heartless to interrupt you.”

“Oh shut up,” Dean mumbled. After a moment, he looked up, a red tinge coloring his cheeks. “Did you need anything?”

“Not really,” Cas said, reaching down to pick up the sponge. He placed it in Dean’s hand, fingertips grazing Dean’s wrist. “I just wanted to spend some time with you. I can come back if you want to be alone”

“No!” Dean spluttered. The red completely suffused his face. “I mean, you can stay if you want. You don’t have to help or anything.”

Cas smiled as he shrugged the trench coat off. “I don’t mind helping, really Dean.”

Dean froze before quickly turning to the shelf and grabbing another sponge. “Here you go, Cas,” he said, dunking the sponge and tossing it to Cas. 

Cas moved too slowly and the sponge struck him in the dead center of his chest. Dean’s mouth dropped open but no words would come out. Cas looked at the wet sponge laying on the floor then up at Dean. Carefully he grabbed the sponge, dunked it into the water and, quick as a whip, tossed it at Dean.

Dean just barely managed to catch the sponge but a spray of water still soaked his old Metallica tshirt. He glanced down at the soaked shirt, then back up at Cas, who was admirably trying to look innocent. He couldn’t hide the twinkle in his eye though. “Oh, it’s on, Cas.” Dean grabbed the bucket and splashed Cas.

Cas laughed and reached for the bucket, causing water to splash back onto Dean. Quickly, Dean pushed the bucket into Cas, catching him by surprise, before backpedalling and grabbing the hose.

“Dean,” Cas growled. “You wouldn’t dare.”

Dean’s eyes sparkled with glee. “You asked for this, Cas. Are you chicken?”

“Dean,” Cas said again, slowly advancing on Dean. 

“Cas,” Dean mockingly growled. He turned the water on, feeling it fill the hose and settling behind the nozzle. Cas rounded the corner of the Impala, feet away as Dean spun the nozzle head to jet. He held the nozzle in front of him, just as he held his Colt in battle. “Just say mercy, Cas. That’s all you have to do.”

Cas lunged at him. Dean squeezed the trigger, instantly soaking the rest of Cas’ button up. Before he realized it, Cas had wrestled the nozzle from him and drenched Dean. The two fought for control over the hose until there wasn’t a dry item of clothing between them. 

Dean looked at Cas: blue eyes sparkling with mirth, cheeks flushed from effort, chest heaving as he fought for breath.  _ Fuck, _ Dean thought.  _ He’s beautiful _ . 

Without thinking, Dean dropped the nozzle and crowded into Cas’ space. Cas’ eyes widened momentarily before he grinned up at Dean. Before he lost his nerve, Dean quickly closed the space between him and Cas, setting a bruising kiss on Cas’ lips. Cas wound his arms around Dean’s neck, pressing himself firmly against Dean.

Groaning, Dean pushed Cas against Baby’s door, trailing a line of kisses across Cas’ stubbled jaw. Before he could trace his way down the column of Cas’ throat, Cas gently pulled him back. “Dean, maybe we should change.”

Dean bit back a whine at the loss of contact. “Change? What do you mean?”

Cas gestured at their wet garments. “I think we should get dry before you get sick.”

Dean actually groaned that time, leaning forward and burying his forehead in Cas’ neck. “Cas, you know how to ruin a moment, dont you?”

Gently, Cas traced a finger down Dean’s spine. Dean couldn’t help the involuntary shiver that rippled down his back. He leaned close to Dean’s ear before whispering, “I didn’t say that we couldn’t change and warm up together.”

Dean pulled back, eyes seeking Cas’. He shivered again, delighting in the heated look Cas was giving him. He yanked Cas towards him, hands knotting in the wet fabric. Before sealing their lips in another kiss, he breathed, “Now that is an excellent idea.”


	23. Day 23 - A Mishap in the Making

**Summary for the Chapter:**

> April 23 - Playing Twister

Leave it to his dorky little brother to pick “Game Night” as a theme for his birthday. If that wasn’t bad enough, Sam had to put “Bring your favorite game” on the invites. Dean shuddered thinking of what some of Sam’s more  _ interesting  _ friends could decide to bring. 

Now, Dean knew he was a nerd and was proud of it. He and his best friend Charlie would LARP and binge Harry Potter and Star Wars until the sun rose. But if someone decides Monopoly was the perfect party game…? Dean shuddered at the thought. He had already put his own choice, Cards Against Humanity, in the center of the den table.

Absentmindedly Dean checked his phone. Sam had thankfully decided to invite some of Dean’s closest friends too. Granted, Charlie and Cas spent so much time at Dean’s house that they practically considered Sam to be their little brother too, but Dean was relieved it wasn’t just going to be Kevin, Chuck, Andy and Gabriel.

Before he could shoot a text to Cas or Charlie to see when they were arriving, he heard Gabriel yelling excitedly upstairs followed by Cas’ signature low grumble. Dean bounded up the steps two at a time.

“Gabriel, I thought I told you to pack Exploding Kittens.” Cas was squeezing the bridge of his nose, eyes closed tightly. 

“Well, yeah you did. But that’s lame. This,” Gabriel slapped the box laying on the dining room table, “is a classic.”

“Please tell me your classic isn’t Monopoly,” Dean said as he entered the dining room.

Gabe shot him a death glare. “As if, Dean-o. That’s lamer than lame.”

Dean peered over Gabe’s shoulder and started laughing. “Twister? Really, Gabe, you think your friends are coordinated enough for Twister?”

A mischievous smile crossed Gabe’s face. “Of course not. That’s why it’s going to be so much fun.”

Dean bent over, laughing.

“Dean, you realize we will also have to play this, right?” Cas grumbled.

Dean straightened, mirth still crinkling the corners of his eyes. “Ya scared to get twisty, Cas? Thought you would be flexible with all of your yoga in the park.”

A tinge of red highlighted the tops of Cas’ ears. “Well, I mean, yeah but…”

Slapping a hand on Cas’ back, dean smiled at him. “Don’t worry about it Cas. You’ll be far from the worst at this game.”

“That’s what I’m worried about,” Cas mumbled to himself. 

⬥⬥⬥

After Charlie had beat them all at Mario Kart and Dean had terrorized the younger kids with Cards Against Humanity, Gabe stealthily slid Twister on the top of the game pile.

Sam reached for the top box, snorting out a laugh when he saw what it was.

“Fine, Gabe, we’ll play Twister if it’ll make you happy.”

Chuck and Kevin both groaned. “Do we have to?” Kevin whined.

“Yeah, we have Clue and a few other games that more people can play,” Chuck agreed.

“If you guys are so worried, me, Charlie, Cas and Sam can go first. Three of us will play and one will call the colors,” Dean stated, grabbing the box from Sam to set up the mat.

Laughing, Charlie grabbed the spinner from Dean’s hands. “I’ll call colors. I don’t want to be squished when you oafs end up falling.” She stretched up on her tiptoes and ruffled Sam’s hair. “Especially this growing Moose.”

“Hey now,” Sam protested, before walking to the edge of the mat.

“Birthday boy can go first,” Dean crowed. “Then Cas, then me”

“Alright!” Charlie called out. “Sam, left foot, green.”

After several rounds, Sam had a left foot on green, right foot on blue, and left hand on yellow. Dean and Cas weren’t much better but they had chosen spaces closer to the other end of the mat. 

Charlie hit the spinner and started laughing. “Alrighty, Sam, you’re going to put your right hand on red.”

“Oh come on!” Sam cried. He stretched slowly towards the back of the mat until he fell with a yelp.

Dean’s body started shaking with laughter until Cas fixed a glare on him and stated, “Keep laughing Dean. Make this win easy for me.”

Dean’s eyes narrowed, his competitive streak flaring up. “Bring it on, Cas.”

Cas gulped and glanced at Charlie. “What do I need to do?”

Flicking the spinner, Charlie called out, “Left hand, yellow.”

Cas gazed at the mat and a strange expression flitted across his face momentarily before he planted his hand beside Dean’s, causing him to almost lay flat on the mat.

“Dean, you’re going to be right foot, red.” Charlie’s eyebrow raised as she studied the mat.

Huffing a breath, Dean studied the mat. There was no way he was going to be able to slide a foot under Cas. He bit his lip before mumbling to himself, “Here goes nothing.” He flung his leg over Cas, causing him to almost straddle Cas’ hips. He could feel the heat rising in his cheeks and was confused but gratified to see Cas’ ears turning red.

Charlie giggled before spinning for Cas. “Oh boy! Cas, can you move your left foot to blue.” Cas groaned before trying to pull his left leg under his right. Inadvertently, his foot nudged Dean’s. 

Dean tried to adjust himself but he felt his leg slipping. Before he could yell a warning, he collapsed on top of Cas. After the shock wore off, he realized he was truly straddling Cas. Charlie let out a piercing wolf whistle.

“Well Cas, I never imagined this is how I would be on top,” Dean blurted out, before slapping a hand across his mouth.

Cas’ mouth dropped open but he quickly pulled himself together and quipped, “Funny you think you’d be on top.”


	24. Day 24 - No More Excuses

**Summary for the Chapter:**

> April 24 - NSFW

**Notes for the Chapter:**

> I'm going to preface this by saying I've never written any type of smut so please, please don't judge this too harshly. It's light smut and I tried my best lol.
> 
> Also, this takes place in an alternate season 9 where Cas did not get kicked out of the bunker when he became human.

Dean always had an excuse. At first, it was the fact that Cas was an angel and clearly not to be trusted. They weren’t even the same species, for crying out loud. Plus, Jimmy was technically in there too and that was just...weird. Dean had shuddered at the thought.

Then, he was with Lisa and trying to figure out what was wrong with Sam. And Cas became Godstiel. Then he died. Blue eyes haunted Dean’s dreams for weeks. 

It wasn’t any better once he came back to life. He saved Sam by taking Sam’s madness and once he was free of that, they were plunged into Purgatory. Dean shivered at the thought of leaving Cas and then Cas being brainwashed by Naomi. 

But now? Cas was gloriously human and all of Dean’s reasons were crumbling. Ezekiel had put up a fuss about Cas staying but he retreated into Sam for the most part. Glancing over at his brother and Cas, Dean couldn’t help his smile. They were drinking at a bar and Cas’ tolerance was ridiculously low. His cheeks were flushed and he had a bad habit of running his hands through his hair as he talked. 

Images of Cas storming into a barn with that phenomenal sex hair filled Dean’s mind. He shook his head. There was no point in thinking like that. He wasn’t going to take advantage of Cas like that. And who knows? Cas probably only liked women. Dean turned back to the bar and ordered another two shots. He was going to need it. 

An hour later, Dean was going crazy. Cas had been inching closer to him all night. Thankfully Sam either hadn’t noticed or decided to not notice. Dean’s heart had raced as Cas sat beside him, leg pressed against Dean’s own. Becoming human hadn’t changed the scent that was just so  _ Cas _ : petrichor and ocean winds and lightning. It was heady and consuming. Dean had to escape to the bar time and time again before he let himself get high on it.

Then, the casual touches began. Sam had suggested Dean start teaching Cas how to play pool so that he could possibly learn how to hustle one day. Dean shrugged and agreed; it was always good to have another potential source of income. He didn’t expect how  _ close _ you had to get to teach someone how to play pool, however. He leaned over Cas’ shoulder, correcting his hands on the cue, straightening his posture. The torture didn’t end once Cas began picking up the game. Dean’s eyes kept sliding down to Cas’ ass. He would rip his gaze away, a blush tinging his cheeks, before he found himself staring again. 

The one thing that Dean hadn’t expected was how affectionate Cas became once he had enough drinks in him. He would grab Dean’s shoulder or arm often and placed a hand on Dean’s back during conversations. After a band began playing live music and normal conversation became difficult, Cas would lean in close to Dean, whispering in his ear. Cas’ hand would stray to Dean’s lower back or waist and Dean would have to excuse himself, desperately needing fresh air. 

The breaking point came when they were playing darts. Dean played an almost perfect game and turned to Cas, triumph shining in his eyes. He was in the midst of raising his hand for a high five when Cas crowded up against him and murmured, “Good job, Dean,” in his ear before gently scraping his teeth against Dean’s earlobe. 

Heat flooded Dean’s body and, before he realized what he was doing, he grabbed Cas’ hand and dragged him to the alley behind the bar. Cas laughed as Dean pushed him against the brick wall.

“What the hell are you doing, Cas?” Dean growled. “Are you just playing games? Are you just drunk? What the hell?”

Cas stopped laughing and just stared at Dean, the long, hard stare Dean remembered from Cas’ days as an angel. A shiver crept up his spine. 

“Do you want this to be a game, Dean? Do you want me to say sorry, that I’m drunk and don’t know what I’m doing?” Cas advanced on Dean, crowding him against the opposite brick wall. “Do you Dean? Would that make this easier? We can go back inside and pretend that I haven’t seen you staring at me all night. I’m tired of pretending that I don’t see, Dean. I don’t have endless time to wait like I used to. I’m human now. So tell me, Dean. What do you want?”

Dean opened his mouth, ready to tell Cas to forget it, to just go back inside and get Sam so they could leave. Instead, he found himself saying, “You.”

Cas tilted his head to the side, confusion evident on his face.

Dean cleared his throat and grabbed Cas’ hips. “I want you, Cas. Hell, I think I always have. I just kept making up excuses but I’m tired, Cas. I’m tired of constantly denying myself happiness.”

Joy shone in Cas’ eyes as he shoved Dean against the wall. He rested his forehead against Dean’s and paused for a moment, staring deeply in Dean’s eyes. Dean knew instinctively that Cas was giving him yet another moment to say no. Instead, he surged forward, capturing Cas’ lips with his own. He licked the seam of Cas’ lips and was ecstatic when Cas parted his lips, letting Dean in. 

Before Dean could fully enjoy making out with Cas, the dark-haired man pulled back. Dean couldn’t quite stifle the whine he let out. A smirk pulled at Cas’ mouth as his lust-darkened eyes raked up and down Dean’s body. He firmly pushed Dean against the wall and slotted a leg between Dean’s as he began tracing a fiery line of kisses down the column of Dean’s throat. A moan ripped its way from Dean as he threw his head back, grinding against Cas’ leg. Arousal raced through his veins as he felt Cas push against him, chasing his own high. 

It was all happening too fast. Dean hadn’t been with anyone in ages and he felt that familiar tightening, blinding high coming on too quickly. He tried to tell Cas but each time he opened his mouth, Cas’ hands moved further south or his mouth discovered a new, sensitive spot on Dean’s body. Finally, he cleared his throat. “Cas,” he moaned. “Cas, we have to stop.”

Cas’ eyes flicked up to Dean, the blue almost completely eclipsed. “No,” he growled, diving back to his task of marking up Dean’s throat. His hands deftly went to the front of Dean’s jeans.

“Cas,” Dean whined, half-heartedly pushing against Cas. In return, Cas rutted against Dean and sank his teeth in the crook of his neck. Heat poured through Dean’s muscles as he came, sagging against Cas. Seconds later, Cas groaned into Dean’s shoulder, pushing them both against the wall for balance.

After catching his breath, Dean pressed a gentle kiss to Cas’ temple. “I kinda hate you right now,” he murmured.

“Hmmph?” Cas questioned unintelligibly. “Was that not good?”

“Too good, Cas. You made me come in my pants like a horny teenager. Did you even think about the fact that we have to go back in the club, get Sam and then drive back like this?”

Cas wearily pulled back, but a smile was firmly anchored on his face. “It’s probably a good thing that there’s two clean pairs of boxer briefs and jeans in the trunk then, isn’t it?”

Dean let out a bark of laughter. “You little shit. You planned this!”

Cas leaned in, placing a quick kiss on Dean’s lips. “Maybe,” he murmured against Dean’s skin. “But do you regret it?”

Dean wrapped his arms around Cas, pulling him in for another bruising kiss.


	25. Day 25 - Lost in the Stars

**Summary for the Chapter:**

> April 25 - stargazing

**Notes for the Chapter:**

> I will admit that I'm a sucker for Van Gogh and the song "Saturn" by Sleeping At Last and this prompt was the perfect time to combine them both. :D

Cas had been lost since he had been cut off from Heaven. Dean saw it in the way Cas listlessly wandered the bunker, the way he looked at you without really seeing you. No matter what Dean tried, Cas just wasn’t snapping out of it. 

Sam had tried to talk to Dean about it. Cas had seen the formation of the world, had watched humanity become what it was today, had been a part of something so grand only for it to get snatched away. He was a boat lost in the middle of a vast ocean. Dean had snapped at Sam. He didn’t need Sam to explain it to him. Wasn’t he the one with the profound bond with Cas? The thought caught sharp and hot in Dean’s mind. What good was a profound bond if he couldn’t even help Cas?

He thrummed his fingers against the table in the war room, deliberating for the hundredth time the ways he could snap Cas out of his own head. He grabbed Sam’s laptop to google who knows what but he stopped short at the starry screensaver. The stars, Dean thought, eyes widening. 

A long-forgotten quote from Van Gogh popped in his mind: “I don’t know anything with certainty, but seeing the stars makes me dream.” A grin tugged at Dean’s mouth as he diligently opened Google and began searching for constellations visible in Kansas.

The next few days, Dean kept checking and double-checking the weather until finally, four days after his idea, all of the forecasts called for a completely clear night sky. He had already mapped out the perfect location, with as little light pollution as possible.

The worst part of this whole adventure was actually getting Cas in the car. Not that it was difficult, by any means. Honestly, the fact that Cas didn’t put up a fuss, just followed behind Dean without complaint, broke Dean’s heart. If this plan didn’t work…

After driving for almost an hour, Dean cut his eyes toward Cas and was gratified to see Cas’ brows furrowing a bit in confusion. The corner of his mouth twitched upwards just a hair. He couldn’t let himself get excited quite yet. 

Finally, they reached the long dirt path Dean had dropped a pin on in Google Maps. He took the path slowly, not wanting to damage Baby in any way.

“Dean,” Cas asked, voice hoarse from disuse, “where are you taking me?”

“You’ll see, Cas. Just be patient.”

Cas huffed, shifting in his seat. Dean started humming along to the radio, thrilled at Cas’ small show of emotion, even if it was frustration. Better than nothing, right?

When the car stopped, Dean hurriedly jumped out and popped the trunk, grabbing the heavy black bag and a folder of papers. He began walking across the field a bit, trusting in the fact that Cas would follow him. Unsurprisingly, when he knelt on the ground to open the bag, Cas wasn’t far behind him.

Dean pulled a large telescope out of the bag. He wasn’t quite sure why the Men of Letters had a telescope but he had stopped questioning the things he found in the bunker a long time ago. Dean glanced up at Cas and saw that Cas was watching him in rapt silence, actually watching him and not the blank staring Dean had sadly grown accustomed to.

“Wanna stargaze, Cas?” Dean softly asked, an unfamiliar shyness taking hold of him. He shook it off, refusing to think about the reasons behind it and adjusted the telescope. Stepping back, he motioned for Cas to look through it.

“You should be able to see Cepheus, Draco and Cassiopeia. And of course Ursa Minor,” Dean rattled off, remembering the constellations he had painstakingly researched. 

For several moments, Cas kept his eye pressed to the telescope, adjusting in minutely. Finally, he straightened and looked at Dean. The look on his face shocked Dean: Cas’ eyes were shinier than normal and he looked like he was about to start crying. 

Dean quickly put his arm around Cas’ shoulder. “Are you okay, Cas? I’m sorry if this upset you. I just figured that you might like to get out of the bunker and look at the night sky. I know that staring at the sky makes me feel like I’m vast and small at the same time. I know it’s not the same as when you were an angel but, I don’t know, man. There’s just something about the sky that’s captivating…” Dean trailed off, realizing he was rambling. 

“Thank you, Dean,” Cas said, gently placing a hand under Dean’s chin, making Dean look him in the eye. “I had forgotten how things could still seem infinite. How it’s rare and beautiful that we even exist.”

The two trekked back to the Impala but, instead of leaving, settled onto the hood, fingers casually laced together as they lost themselves in the intricacies of the night sky.

**Notes for the Chapter:**

> For some reason, I love writing from Dean's perspective and I've been a sucker for hurt/human Cas lately. Oh well :P


	26. Day 26 - The Sweater Tells the Tale

**Summary for the Chapter:**

> April 26 - Ugly sweaters

**Notes for the Chapter:**

> Sorry if there are any typos/grammatical errors. I typed most of this on my phone and sometimes it autocorrects words weirdly.
> 
> Also, I struggled a little with what I wanted to do with this chapter so my apologies if it drags a little! There's absolutely no plot or anything -_-

Dean’s phone buzzed incessantly on the kitchen counter. Ignoring it, he continued shaping burgers from the heap of hamburger meat. A few seconds later, the buzzing started anew. Dean huffed a breath as he held his hands aloft and walked over to his phone. Sam’s face stared up at him. 

Dean shook his head. “This had better be important,” he grumbled, bending towards the counter and swiping the screen with his nose. Immediately he hit the speaker button. “What’s up Sammy?”

“Okay, first off, this was not my idea,” Sam said in a rush. 

A scowl started forming on Dean’s face. “What are you talking about?”

A feminine laugh came across the line. “What Sam is trying to do is say you shouldn’t get mad at him for what he’s about to ask you,” Jess, Sam’s girlfriend of two years, said.

The lines on Dean’s face smoothed a little. “Alright blonde, what torture have you planned now?”

“Well,” Jess began, “we were talking about wanting to actually create traditions since you guys never really had any holidays growing up. So I thought we should have a Christmas party with all of our friends.”

Dean had finished forming the patties and washed his hands while Jess talked. “Well that doesn’t sound bad. What’s the problem with a party Sam?”

Sam heaved a sigh. “Tell him the rest.”

“So it wouldn’t be a true Christmas party without ugly sweaters! And before you start Dean Winchester, you can suck it up for one night. Plus, we’ll have more eggnog and whiskey than even you could drink in a night.” 

Dean chuckled to himself, knowing Jess was probably standing beside Sam, arms braced on her hips. The woman was a spitfire and didn’t take attitude from either of the Winchester men.

“Fine, fine. You just have to promise me one thing, Jess: Sam’s sweater has to light up.”

Jess let out an almost evil cackle. “Will do!”

The front door opened and Dean could head Cas and Gabe arguing back and forth as they entered the house. As the two filed into the kitchen, Jess yelled out, “Ugly sweater party, our house, next Friday. Make sure Dean actually wears a sweater, Cas.”

“Ugly sweaters?” Cas’ brow wrinkled in confusion followed by Gabe’s whoop of happiness.

“This is going to be great! I’ve been wanting to go to an ugly sweater party for years. Oh, Cassie, I have the perfect sweater for you. Trust me!” Gabe fist-pumped.

Dean bit back a laugh at Cas’ tortured expression. Sam really should have been apologizing to Cas and not him. Clapping a hand on Cas’ shoulder, he said, “Don’t worry, Cas. It’s just one night.”

Gabe had already left the kitchen but he yelled back, “All it takes is one!”

The day of the party, Gabe had swung by Dean and Cas’ apartment and all but kidnapped Cas with the excuse that Cas’ sweater needed to be a surprise. Shortly thereafter, Dean threw his sweater and other party necessities in a bag and headed to Sam and Jess’ house to help with setup.

About thirty minutes before guests were to arrive, Dean changed into his sweater. He stood in front of the full-length mirror on the guest room’s closet door and chuckled at his choice. He had borrowed Charlie’s LARP costume supplies and attached a half naked Ken doll to a black sweater along with a candy cane-striped stripper pole and homemade dollar bills. Felt letters spelling out “On the naughty list” had been glued beside Ken. After double-checking the glue, Dean strolled out to the living room where he burst into laughter.

Jess was dressed like a Christmas mantel, complete with stockings and a fake fire. But Sam’s outfit was what had tears coming to Dean’s eyes. Jess hadn’t disappointed him with his lighted sweater request. The majority of the sweater was plain red except for a large white lit Christmas tree. The real kicker was the two giant glittery Christmas ball ornaments that dangled off the bottom of the sweater.

“Keep laughing it up Dean,” Sam griped as the doorbell rang. Dean’s laughter changed to snorts as he heard the ornaments gently tapping as Sam walked.

Charlie and Jo were the first to arrive in matching red sweaters decorated with gingerbread men and the words “Bite me.” A few minutes after them Benny showed up, a felt dartboard and velcro darts attached to his sweater.

Just as Dean was about to text Cas and ask where they were, Gabe strode into the living room. His sweater was fairly simple: an elf was plastered over the front but instead of a face, there was a mirror. 

“Real cute, Gabe,” Dean smiled. “Where’s Cas?”

“He should be in soon. I think he’s a little embarrassed.” Gabe smirked. 

Dean’s attention was drawn to a burst of laughter from Jess. When he turned, he saw Cas standing in front of her, face as red as the girls’ sweaters. Dean craned his head, trying to see Cas’ sweater, but Sam soon joined Jess blocking Cas completely from view. Gabe gently pushed Dean forward. “Go see the masterpiece I created, Dean-o.”

Dean glanced at Gabe, worry creasing his brow, but he quickly walked toward Cas. His mouth dropped open as he took in Cas’ sweater. Gabe had truly gone all out: tinsel lined the edges of the navy sweater as well as formed a horizontal line across Cas’ chest. A red sock, a beer can, and jingle bells dangled from the tinsel. What had shocked Dean was the fact that large green letters spelled “HUNG” across the top. 

Laughter began bubbling up in Dean’s chest. “Well, Cas, I don’t know whether to congratulate you or help you take revenge on Gabe.”

“Maybe you can enlighten me on what landed you on the naughty list,” Cas’ eyes sparkled.

“I, well I,” Dean spluttered.

“Come on,” Cas laughed. “Let’s go get some of the eggnog Jess promised us.”


	27. Day 27 - Lessons From Movies

**Summary for the Chapter:**

> April 27 - Romantic Movie Kiss

**Notes for the Chapter:**

> This chapter completely ran away from me and wouldn't stop at 1000 words ;D

Even after Cas got his grace back, he continued indulging in Netflix binges. When Sam and Dean were asleep, there wasn’t much to do around the bunker if you didn’t want to read the hundreds of books gathered there. 

It was during one of these Netflix binges that Cas fell into the rabbit hole of rom-com movies. After watching two characters admit their love for the twenty-fifth time, everything clicked into place.

Cas loved Dean.

A thousand moments flashed through his mind: Meg’s comments about the two, how Dean broke through Naomi’s brainwashing, Dean telling Cas that he needed him, Dean not wanting to leave Cas in Purgatory, Cas deciding to give up an army for Dean… How did he never realize it before now? He always chalked it up to their profound bond but was that just an excuse? 

Once the realization sunk in, Cas made his mind up: He needed to tell Dean how he felt. But he knew more than almost anyone that Dean didn’t indulge in “chick flick moments.” So, he needed to test the waters a bit. His eyes flicked back to the screen and a smile pulled at his lips. Why not use everything he had been learning from his Netflix binges?

The first opportunity presented itself after their next hunt. Cas and Dean had been investigating a nest of vamps and were taken by surprise after questioning the medical examiner. Dean’s fed suit jacket and shirt were destroyed in the fray and he had griped about how “his favorite jacket” was “absolutely ruined, Cas, it’s a tragedy.”

Pulling his wallet out, Cas handed several bills to Dean.

“What are you doing?” Dean questioned, staring at the money in Cas’ hand.

“You need to buy yourself some new clothes,” Cas stated matter-of-factly. “Something conservative and not too flashy.”

Dean cocked an eyebrow and pushed Cas’ hand down. “Dude, that’s what fake cards are for. Don’t worry about buying me clothes.”

A few days later, all three of the men were sitting in the bunker’s library. Sam was cataloguing books while Dean was supposedly searching for potential cases. Cas deliberated a few moments before he looked up at Dean.

“Dean, what’s something on your bucket list?”

A pencil fell from Dean’s hand. “My what now?”

“Your bucket list,” Cas said. “The things you want to do before you die. We’re in between cases right now and I thought maybe we could do something on your bucket list.”

Dean scoffed. “Cas, I don’t have a list of things I want to do before I die. There’s no point with this job.”

Cas looked down at the table and fiddled with the notebook in front of him. “Okay, Dean.”

After two failures, Cas had started to get a little disheartened. Maybe he wasn’t picking good enough movies to learn from. That had to be it, he decided. Googling “best romantic movie” helped him settle on a new plan. 

The next day, Cas and Dean left the bunker to deal with a small hunt, while Sam stayed behind to look up some lore for Donna and Garth. Cas had snuck a sketchpad and some pencils in the front seat while Dean loaded their bags in the Impala’s trunk. After they had been on the road for almost an hour, Cas pulled the sketchpad onto his lap and angled himself towards Dean.

“Whatcha doing buddy?” Dean asked, glancing over at Cas.

“I discovered I have a talent for drawing. It’s very soothing,” Cas said, flipping the pad open. “Do you mind if I sketch you, Dean?”

A faint flush tinted Dean’s face. “I mean I guess that’s okay. It’s whatever you want to do, Cas.”

Cas hummed happily and began sketching the basics of Dean’s profile. Tension was evident in Dean’s shoulders and neck at first until, little by little, he relaxed under Cas’ gentle gaze. 

When they reached their destination, Dean held his hand out and Cas placed the pad on it. Dean studied the sketch, the same flush staining his face. “It’s good, Cas. Really good.” He gave Cas a small, unsure smile when he handed it back.

_ Small steps _ , Cas thought.

His next move was digging an old boombox out of Jody’s garage. He had tried to come up with an excuse for why he specifically needed a boombox but she just laughed and told him she had seen her share of 80s’ movies. Biding his time, he waited until Sam had left for an evening run. Ever so casually, he slipped a tape into the boombox he had placed in the corner of the war room and pressed play. 

Peter Gabriel’s “In Your Eyes” filled the room. After a moment, footsteps could be heard coming from the bedrooms. 

“Cas? What are you playing?” Dean’s voice drifted into the war room before he made an appearance.

_ "And all my instincts, they return. And the grand facade so soon will burn _ ,” filled the air as Cas deliberated on how to answer.

“I heard this song and liked it. It’s a nice song, isn’t it Dean?”

Dean’s lips twitched. “It’s okay I guess. Not Zeppelin though.”

Before Cas could say anything else, Dean had fled the room.

There was nothing left for Cas to do but to pull out the big guns as the saying went.

“What the hell?” Dean griped, slamming his hands on the steering wheel. The Impala has shut off with no warning with Dean just managing to coast onto the side of the road safely. “I just gave her a tuneup last weekend. There shouldn’t be anything wrong.”

“Maybe you need gas,” Cas mused. “There’s a gas station a quarter mile up the road.”

“Yeah but who wants to walk in this rain?” Dean featured to the rain sheeting down outside.

“It’s only going to get worse. We should go now,” Cas stated. 

The two dashed out of the Impala, running up the side of the road.

“Dean!” Cas yelled. 

Barely turning, Dean saw Cas standing stock still.”

“What the hell, Cas? We’re getting soaked out here.” Dean’s jacket was doing a poor job of shielding his head as he held it above himself. He would have kept running but Cas had the gas can clutched in his right hand. 

“Isn’t that the point?” Cas slowly moved toward Dean, dropping the gas can.

“What are you playing at, Cas?” Dean yelled.

“I’ve been oblivious all these years Dean but I’m an angel. That’s my excuse, pitiful though it might be. I didn’t understand what all of this,” he threw up a hand between the two of them, “was but you? You should have known. Once I started connecting the dots it was so painfully obvious Dean.”

“What, Cas?” Dean’s face looked panicked. “Tell me what’s so obvious that we have to talk about it in the rain.”

“I gave up an army for you, Dean. I always come when you call. I bend over backwards to help you no matter what. And you! You saved my trenchcoat when you thought I died. You broke me out of brainwashing that no one should have been able to get through. Time after time, we have sacrificed for each other and for what? If you only did it because you care for me like a brother, then tell me and I’ll drop it and we can pretend that nothing happened. But I have to know.” Cas looked at Dean, pleading with his eyes.

“Cas, I..what do you want from me? Why did you decide that we needed to talk about this now? Can’t it wait,” Dean froze, pieces falling into place. “Did you sabotage the Impala?”

Cas’ eyes flicked to the side but, before he could answer, Dean barreled on.

“You did! And the rain,” his mouth dropped. “You sketched me the other day. Then you played the Say Anything song.” Cas’ eyebrows raised and Dean shrugged. “It’s a good movie, Cas. And now, we’re caught in the rain…” his eyes softened. “You set all this up. I don’t know whether to kill you or kiss you.”

“I’d prefer the second one,” Cas mumbled. “At least that’s what Noah and Allie did.”

Dean laughed and walked over to Cas, grabbing the trenchcoat in his hands. “You idiot.” He grabbed Cas’ head and murmured, “It still isn’t over,” right before he kissed him.

Cas had never understood what the movies meant by fireworks or butterflies when you kissed someone. The times he had kissed Meg and April were nothing like that. But this kiss? All of time had slowed for this one moment. The raindrops landed on their faces, slicking their hair to their scalps. Dean’s hands were warm as he cradled Cas’ face in his hands. Delight surged through Cas and he fisted his hands in Dean’s hand, pulling him in tighter. 

The two kissed for what felt like hours before finally breaking apart. Dean leaned his forehead against Cas’ and whispered, “You have bewitched me body and soul.”

Cas’ eyes lit up and he chuckled. “Pride and Prejudice, Dean?”

“Shut up, it’s a good movie. A classic,” Dean said before leaning in and kissing Cas again.


	28. Day 28 - He's Dead Too

**Summary for the Chapter:**

> April 28 - Death

**Notes for the Chapter:**

> I am so sorry.
> 
> Also, I wasn't sure whether to use the Major Character Death warning because this follow canon...but check the end note for this day's spoiler if you're worried about that temporary character death and canon compliant death tag.

“He’s dead, too.”

Those three words kept reverberating through Cas’ head ceaselessly, an ocean wave that ebbed and flowed without fail.

“He’s dead too.”

The three words that Cas knew would be true one day but he could always hope they wouldn’t be. After all, how many times had Cas escaped death? Why couldn’t Dean come back too? He was the righteous man after all. Why did Cas deserve to be saved again and again if Dean couldn’t be?

“He’s dead too.”

Cas felt a part of him shatter. This didn’t make any sense. He hadn’t hurt this bad when he had seen his brothers and sisters die. There were countless numbers of people that Cas had watched die over the years, including several people he cared about, and none of them had hit him this hard. 

“He’s dead too.”

They had locked Metatron away and he wandered away from Hannah’s questions about his grace. Memories overwhelmed him and he sank to the floor, tipping his head back with eyes closed as the scenes flashed before him.

Wide green eyes stared up at him, a knife in his chest, disbelief etched across Dean’s face. The first time Cas interacted with him outside of Hell. “Why would an angel rescue me from Hell?” Cas had told him it was because God had commanded it, that the angels had work for him. He scoffed at that now.

“So, what, I'm Thelma and you're Louise and we're just going to hold hands and sail off this cliff together?” Cas half-snorted at Dean’s reference now. He understood it too little, too late.

“Don’t ever change.” Cas still didn’t know what Dean had seen when Zachariah had flung him into the future but those words? Those words meant everything to Cas.

“Don’t make me lose you too.” One of the first times Dean had truly pleaded with Cas. The souls had clouded Cas’ judgment and made him callous and unfeeling. But looking back made the emotions sharper, stabbing Cas over and over. The fear in Dean’s eyes...A tear slid down Cas’ face.

“I’d rather have you, cursed or not.” Dean always forgave him. He might blow up and rail at Cas but he always forgave in the end. “I’m sorry,” Cas mumbled under his breath. “I should have been there. I should have stopped Metatron before, before…” His words were lost in a choked sob.

“Let me bottom-line it for you. I’m not leaving here without you.” But you did Dean. I forced you to leave then and you’ve left me now. You left without me.

“I need you.” Dean had clutched Cas’ trenchcoat, pleading with Cas, telling him, “This isn’t you.” But it was that “I need you” that broke Naomi’s hold on Cas. But Dean was wrong. Cas was the one who needed Dean. “I need you,” he chanted to himself, tears streaming down his face. “You can’t be gone. I…” he paused, clarity making his thoughts crystal clear. “I love you,” he whispered.

**Notes for the Chapter:**

> Basically this is what I imagined Cas' thought process would be like when Metatron killed Dean at the end of season 9. Technically Dean died but, as we all know, he's not really dead. Hence the uncertainty when it came to tags. I do apologize if the lack of tags or the wrong tags upset anyone!


	29. Day 29 - Can't Fight

**Summary for the Chapter:**

> Day 29 - Karaoke night

When Sam found out the reason Dean hated karaoke, he had vowed to change it.

“Dean, so what if you sang karaoke as a demon? It’s all the more reason to make better reasons to replace those,” Sam argued with Dean.

“I vowed no more karaoke, Sam.” Dean took a swig of his beer.

Sam chanced a glance down the hallway and softly said, “Dude, Cas really wants to go. He was going on about how Claire and Alex went the other weekend and how they said it was so much fun.”

Indecision flashed on Dean’s face. “Fine,” he growled. “But I’m only singing what I want to sing and only one song.”

Holding up his hands, Sam laughed. “I won’t argue. Let me go tell Cas.”

Later that night, Dean quickly threw back two shots. Sam has convinced him to go first to set a good example and Dean had to admit that Cas did look a bit queasy.

“Next up is Dean singing ‘Ramble on’ by Led Zeppelin. Let’s give it up for him!” The cheery blonde handed the mic off to Dean.

Smiling, he began singing, goofing off and purposefully hitting a few wrong notes. A small smattering of applause accompanied him off the stage. 

When he got back to the table, Cas was gone. Before he could even open his mouth, Sam piped up, “He said he was going next.”

Cas was huddled by the side of the stage with the announcer. She smiled as she handed him the mic and flapped her hands at him, as if to encourage him to go ahead. 

Clearing his throat a little, Cas spoke into the mic, voice deeper than normal, “I came across this song a few weeks ago and it spoke to me. Maybe it’ll do the same for you.”

Music began playing softly and Dean was lost as Cas crooned, “The strands in your eyes that color them wonderful stop me and steal my breath. And emeralds from mountains that thrust towards the sky, never revealing their depth.”

Dean’s attention never strayed from Cas for the duration of the song. As the last notes faded, Dean turned to Sam, a wide panicked expression in his eyes. “Did you know?” he whispered hoarsely. “Is that why you pushed me to come out tonight?”

Sam nodded. “Are you okay, Dean?”

Without answering, Dean fled from their booth. Sam dropped his head in his hands. It was just like his brother to run as soon as someone started showing emotion. Cas wasn’t going to take this well. Sam had already had to cajole him into even admitting his feelings at all. After this, Sam wouldn’t be surprised if Cas fled the bunker for awhile.

Lifting his head, Sam watched Cas near their booth and saw his eyes and shoulders drop when he noticed Dean’s absence. Just as Sam was about to try to reassure Cas, a shaky voice spoke into the mic. 

“Hey everyone. I know I sang already but I didn’t really take it seriously or give it my best. So, I wanted to do this again. For my best friend.” Dean clutched the mic, fighting waves of nausea. He concentrated on the opening notes of the song and closed his eyes as he began singing.

“I can't fight this feeling any longer and yet I'm still afraid to let it flow. What started out as friendship, has grown stronger. I only wish I had the strength to let it show.” Dean poured every feeling he had ever repressed in the song. He knew he was shit at expressing his feelings but he also knew that Cas deserved more than a “you too” or “you’re awesome, Cas.”

He didn’t look up until he got to the second verse and deliberately changed the “girl” to “boy.” Cas’ eyes were shining brightly as he listened to every word pouring from Dean’s mouth.

As he sang the last “I can’t fight this feeling anymore,” the entire bar erupted into applause. Dean stumbled off of the stage and straight into Cas’ arms. 

“Did you mean it?” Cas whispered, a sliver of fear hiding in the brilliant blue.

“Every line,” Dean murmured, leaning his forehead against Cas’.


	30. Day 30 - Damnatio Memoriae

**Summary for the Chapter:**

> April 30: Do what you want

**Notes for the Chapter:**

> I won’t lie, I got a little inspiration from Teen Wolf for this.

They had known this coven of witches was powerful, but they didn’t realize how powerful they were. If they had been smart, Cas thought, they would have consulted with Rowena. Maybe there was nothing she could do but they wouldn’t know that now, would they?

By the time Cas had figured out these witches were powerful enough to mask their strength from an angel, it was already too late. They have divided into two chanting groups: one that was working some type of spell and the other chanting protective spells so the first group could complete their ritual.

Dean had charged head-first towards them, two guns loaded with witch-killing bullets. Before he could get a shot off, an invisible force knocked him to the ground. Sam and Cas had tried to sneak past them but to no avail. Cas saw the blonde-haired witch in the middle of the ritual group sneak glances at Dean. As the chanting increased in speed and volume, she had fully directed her gaze toward Dean. Without a second thought, Cas darted in front and the spell hit him square in the chest.

At first, he didn’t think anything had happened. The second group of witches had knocked Sam out as well as Dean and they quickly fled the premises. It wasn’t until Cas rushed to Dean and tried to wake him that the truth sunk in.

Cas was intangible.

_ No need to panic _ , he thought.  _ Sam and Dean are smart. They’ll see I’m not here and they’ll figure it out. _

Dean stirred. “Sammy, you okay?”

A groan rose from the opposite side of the room. “Yeah, Dean. I think the witches all escaped.”

“Yeah, they did,” Dean scanned the room. “At least we both made it out okay.”

_ What about me _ ? Cas wondered.

Sam struggled to his feet and grabbed his weapons. “Well, let’s go back to the room and regroup. Maybe we should call in reinforcements. I think this coven is too big for just us two.”

Panic began overwhelming Cas. Dean followed Sam out the door but paused in the doorway. “Sam,” he called over his shoulder, “do you feel like we’re forgetting something?”

Weeks went by and there was only one thing Cas was sure of: Whatever spell the witches had used basically wiped him from existence. For some reason, if he got separated from the brothers, all he had to do was think about Dean and he was suddenly there with him. He paced the halls of the bunker, ignoring the door that used to lead to his room. The first day he walked through the wall only to see an empty room that looked as if it hadn’t been touched in years.

From Dean’s room, he heard slight whimpers. Gliding through the door, he paused by Dean’s bedside. The man was tossing and turning, eyes darting behind closed lids. Cas wished he could reassure Dean or at the very least see what was troubling him.

Suddenly, the man sat up with a start. “Blue,” he gasped. “Angels and blue and trenchcoats?” He shook his head. “What the hell is happening to me?”

Hope surged in Cas. Was Dean somehow dreaming about him? Did that mean he wasn’t truly forgotten after all?

The next morning, Cas paced in the kitchen, hoping against hope for more information. Dean had just finished making a fresh pot of coffee when Sam strolled in from his morning run.

“Hey Sammy,” Dean said, handing a cup off to Sam. “I have a question for you.”

“What’s up?” Sam leaned against the counter, studying Dean.

“How can you tell if you’ve forgotten something?”

Sam’s eyes narrowed. “It’s a little early for philosophical questions, isn’t it? What brought this on?”

Dean scrubbed a hand through his hair. “Ever since that failed witch hunt, I’ve been having dreams. Weird dreams. They’re full of this bright blue and dark-haired men in trenchcoats. I’ve also dreamed about angels. But not angels like we know. This angel is,” Dean paused, searching for the right word. “Well, he’s nice. There’s no other word for it. I can never see his face though. But there’s this feeling of safety and home.”

Sam was silent for a long moment. “The only thing I can think of is to either summon an angel.” Dean scoffed but Sam continued, “Or we can ask Rowena to consult the book.”

“Much as I hate to admit it, Rowena is the better option. Can you call her? Tell her to get here as quickly as possible and I’ll personally owe her.”

Sam’s eyebrows raised but Dean had already spun on his heel and marched toward the garage.

Rowena hummed as she studied the book. Her gaze kept flicking back to Dean. “You’re lucky you came to me, although I wish it had been earlier,” she finally said.

“Why?” Dean blurted out.

“There’s a trace of something around you. What is your history with angels?” Rowena stood before Dean, studying him.

“What does that..?” Dean cut himself off. “I was supposed to be Michael’s vessel but we avoided the apocalypse.”

“How?” Rowena probed.

“Well, Sammy did become Lucifer’s vessel but I...I didn’t.” Dean turned to Sam. “What stopped me?”

Sam’s face twisted in confusion. “I’m not sure.”

“I feel there are a lot of questions you can’t answer now,” Rowena mused. “Think about your history. What spots seem odd to you?”

“The Leviathans,” Dean said. “How did they get out? I know Crowley helped but he couldn’t have done it alone.”

“What about the angels falling?” Sam chimed in.

Dean could feel his head pounding. With each question he thought of, he could feel his headache worsening. Blue eyes flashed in his mind along with one single thought.

“How did I get out of Hell?” he said. Sam and Rowena turned to each other, confusion marring their features.

Dean paced back and forth frantically. Cas was on the verge of screaming. They were so close, so very close. Without thinking, he darted into Dean’s path. 

Cold suffused Dean’s body. He froze as a name resurfaced.

“Castiel.”

Brilliant light filled the war room as Dean, Sam and Rowena covered their eyes. When it faded, Cas stood before them.

“Bloody hell,” Rowena whispered. “How did you forget the angel?”

“Damnatio memoriae,” Cas croaked. “They erased me from existence. But Dean couldn’t quite forget me and managed to drag me back.”

During this exchange, Dean stood stockstill, staring at Cas. When Cas said his name, Dean rushed over to him and embraced him.

“Never do that again,” he mumbled into the other man’s shoulder.

**Notes for the Chapter:**

> Well, we've finally reached the end! It took me a little longer to do this 30 days challenge but I'm so glad I decided to do it. I've loved every minute of it and plan to continue writing. 
> 
> I'm mulling a few ideas for fics in my head right now, including one loosely based on Legally Blonde. (I'm a sucker for movie AUs.) I'm also planning on possibly doing a few short drabbles every now and then when I see an interesting prompt just to keep myself in practice. 
> 
> I hope you enjoyed reading these 30 days and if you want to chat (or possibly yell at me to write), follow me on [Twitter](https://twitter.com/krislmart). I'm trying to make sure I'm more active up there :)


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